


Everyone Experiments in College

by TVTime



Category: Teen Wolf (TV)
Genre: Adopted Isaac, Alternate Universe - College/University, Alternate Universe - No Powers, Anal Fingering, Anal Sex, Ass Play, Barebacking, Bottom Isaac Lahey, Bottom Scott McCall, Bottom Stiles Stilinski, Brotherly Affection, Brotherly Love, Brothers, Butt Plugs, Cock Rings, Come Sharing, Come as Lube, Daisy Chaining, Dildos, Dirty Talk, Drunk Isaac, Drunk Scott, Drunk Stiles, Explicit Consent, Explicit Sexual Content, Extremely Responsible Consent, Extremely Versatile Sex, First Time, Fluff, Fluff and Smut, Fluid Sexuality, Friendship/Love, Humor, M/M, Making Out, Multi, Multiple Orgasms, Oral Sex, Porn with Feelings, Rimming, Scott McCall & Stiles Stilinski are Brothers, Self-Discovery, Sexual Experimentation, Sibling Love, Sloppy Seconds, Smut, Step-Brothers, Step-Sibling Incest, Threesome - M/M/M, Top Isaac Lahey, Top Scott McCall, Top Stiles Stilinski, Versatile Isaac Lahey, Versatile Scott McCall, Versatile Stiles Stilinski
Language: English
Status: Completed
Published: 2016-11-18
Updated: 2017-01-25
Packaged: 2018-08-31 16:21:14
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 4
Words: 22,221
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8585431
Author URL: https://archiveofourown.org/users/TVTime/pseuds/TVTime
Summary: He smelled like tequila shooters and Isaac, and Stiles liked both those things very much. “I love you,” he whispered, his mouth almost against Isaac's but not quite. Isaac smiled a big goofy grin and wrapped his arms around Stiles. His face slid across Stiles' until he was whispering in his ear, “I love me too.”Stiles quirked an eyebrow and pulled back enough to look at Isaac. “You mean you love me or you love you?”Isaac turned the question over in his head, trying to make sense of it before answering. “I love both of us. And Scott,” he added, his head rolling back onto Scott's shoulder. “Ooh and ice cream.”“What?” Scott asked, catching just the tail end of that.“I love you and ice cream,” Isaac answered, grinning up at him.Scott smiled back and carded his fingers through Isaac's hair again. “I love you and ice cream too.”





	1. Love and Ice Cream

**Everyone Experiments in College**

**Part 1: Love and Ice Cream**

 

Isaac laughed at nothing in particular as he lay his head on Scott's shoulder. Everything was a little bit spinny, and a lot funny.

 

“You. Okay?” Scott asked, his words clear and coherent, if a bit slow. He placed his hand on Isaac's left thigh and gave it a gentle squeeze.

 

Isaac raised his head, grinning as the wobbly, happy feeling hit him again. He scrunched up his mouth as he answered. “Great!”

 

Stiles laughed from Issac's other side and waved his hands expansively. “He's grrrreeeeeaaaatttt!”

  
The three of them cracked up as Stiles collapsed across Isaac's and Scott's laps, making himself comfortable as Scott started stroking his hair and Isaac folded his hands on Stiles' stomach, thumbs languidly messaging him through his shirt.

 

“Fun night, guys?” Danny, their Uber driver, asked from the front of the car.

 

“Grrrreeeeeaaaatttt!” They all declared in unison before dissolving into another fit of laughter.

 

Isaac decided Stiles had the right idea as he collapsed against Scott's chest, his head now on Stiles' shoulder.

 

Scott let go of Stiles' head with one hand so that he could drape an arm around Isaac, holding them both at the same time.

 

“So, I have to ask, who's dating who?” Danny inquired, chuckling at their antics as he watched them in the rearview mirror.

 

“Oh we're all best _best_ friends,” Isaac answered, squeezing Stiles close with one hand and clumsily reaching back with the other to pat Scott's chest.

 

“And. Roommates,” Scott added for emphasis. “And. And brothers.”

 

“Not bioblogical blothers though,” Stiles clarified before stage whispering to Danny, “I'm blisexual.”

 

“Dude, you've got too many L's,” Isaac told Stiles, sitting up a little bit and giving him an overly serious look.

 

“Whaz an elle?” Stiles asked, reaching up and rubbing Isaac's throat. He was warm. And pretty.

 

“An L,” Issac answered, furrowing his brow. “You know, an L!”

 

Stiles shook his head. He didn't know.

 

Isaac huffed, exasperated. “Scott, tell him abou-about the L's”

 

Scott nodded, running a hand through Isaac's hair to let him know he was on the job. “Stiles. Stiles, listen.”

 

Stiles' looked up, past Isaac, and into Scott's soft brown eyes. He was pretty too. _Scott and Isaac should make out_ , Stiles decided. He'd like to see that.

 

“The L's are. Are in your. Your mouth,” Scott told him.

 

“My mouth?!” Stiles asked, horrified.

 

The other two boys nodded jerkily.

 

Stiles giggled. “I want to get you in my mouth.”

 

Scott gave him a confused look. “Which. One of, one of, of...”

 

“Of us!” Isaac interjected with a finger wave, proud of himself for helping Scott.

 

“Yeah. Of us. Are you talking to?” Scott asked.

 

“Indeed,” Stiles answered, nodding meaningfully and tapping the back of Danny's seat like he was sharing an inside joke.

 

Scott chuckled and Isaac pulled Stiles closer against his body. Soon they were both snoring lightly, leaving Stiles the last one conscious in the car with Danny.

 

Stiles played with Isaac's fingers for a little while, but eventually grew bored and sat up.

 

“So you're not really brothers?” Danny asked for clarification, looking at Stiles in the rearview again.

 

Stiles shrugged at him before taking off his jacket and draping it over Isaac's chest. “We sorta are, just not bly blood. Me and Scott – always been blest fliends. But then when we were like flourteen my dad and his mom got mallied. So we're step blothers. Then the next year my dad, my dad...uh what was I slaying?”

 

“About Isaac joining your family,” Danny prompted.

 

“Oh right. My dad answered this domestic displute case. Heza sheriff. Anyway, Isaac's old dad was...” Stiles frowned and gave Isaac's knee and shoulder a squeeze. “Anyway we adopted him and stuff. He's our adopted bro.”

 

“It looks like you're all really close,” Danny said, smiling at Stiles in the mirror.

 

“We are. Like _sooo_ close. When we were kids, I useta be really jealous if other people played with Scott. But like, Isaac...” Stiles shook his head, smiling affectionately at his adopted brother. “It's okay for Isaac to play with Scott. 'Cause he's Isaac, you know.”

 

Danny nodded. “Yeah I see.”

 

“I just wish I could, you know, _plaaaay_ with them,” Stiles said, before leaning over and whispering to Danny too loudly for it to actually be a whisper. “I mean their penises.”

 

“Yeah, I got that,” Danny answered, fighting back a laugh.

 

“Do you think that's weird?” Stiles asked, eyebrows knitted together in worry.

 

“Nah, they're really hot, and you guys aren't biological brothers. It's fine.”

 

Stiles nodded, agreeing with Danny's assessment. “Yeah, plus I just, like, love 'em so much, and I do suck a pletty mean dick if I do slay so myself. I wanna do that floor them.”

 

“Have you offered?” Danny asked.

 

Stiles shook his head, accidentally banging it into the window in the process. “Nope. I didn't wanna make things weird. But me and Scott useta blow each other when we were younger. So I think he'd still want to.”

 

“Are either of them gay or bi?” Danny asked.

 

Stiles shook his head again, this time eying the window suspiciously like it was going to attack him. “They're straight. But I don't wanna date them – that'd be weird – I just wanna mess around, have some fun, make 'em feel good. That typa thing.”

 

Danny shrugged. “You should go for it. They seem like pretty open guys. I bet it's something you'd all enjoy.”

 

Stiles nodded, losing himself in thought and eventually slumping down against Isaac and Scott again.

 

“I think this is your stop,” Danny said a little while later as he pulled up in front of the address he'd been given.

 

Stiles grinned and reached into the front seat, wrapping his arms around Danny. “I like you.”

 

“I like you too,” Danny answered, patting Stiles' hands around his chest.

 

“Do you want my number?” Stiles asked.

 

Danny considered the question for a few moments, wondering if he wanted to get involved with Stiles and by extension this complicated but seemingly nice group of guys. Eventually he decided to go for it. “Yeah sure. Call it out and I'll text you.”

 

Stiles gave Danny his number and they exchanged a few quick texts and talked about getting together and going out some time before Stiles woke his two non-biological brothers and wouldbe lovers.

 

“Are we. Here?” Scott asked, opening his eyes and blinking as he looked around.

 

“If we aren't here, where would we be?” Isaac asked, philosophically.

 

“But we are here,” Stiles pointed out.

 

Isaac turned and leaned his forehead against Stiles'. “Exactly,” he whispered, warm breath ghosting across Stiles' face.

 

He smelled like tequila shooters and Isaac, and Stiles liked both those things very much. He had to remind himself it wouldn't be okay to just lean in and kiss him. “I love you,” he whispered instead, his mouth almost against Isaac's but not quite.

 

Isaac smiled a big goofy grin and wrapped his arms around Stiles. His face slid across Stiles' until he was whispering in his ear, “I love me too.”

 

Stiles quirked an eyebrow and pulled back enough to look at Isaac. “You mean you love me or you love you?”

 

Isaac turned the question over in his head, trying to make sense of it before answering. “I love both of us. And Scott,” he added, his head rolling back onto Scott's shoulder. “Ooh and ice cream.”

 

“What?” Scott asked, catching just the tail end of that.

 

“I love you and ice cream,” Isaac answered, grinning up at him.

 

Scott smiled back and carded his fingers through Isaac's hair again. “I love you and ice cream too.”

 

“Do we have ice cream?” Isaac asked hopefully.

 

Scott stared off into the middle distance. “I dunno.”

 

“You guys should probably go in and check,” Danny said, chuckling and unlocking their doors.

 

Scott nodded. “That's a good idea.” Then he leaned over and tried unsuccessfully to whisper to Stiles. “I like him. He's smart. Did you get. His number?”

 

“Uh huh. I put it in my phlone,” Stiles answered, reaching backward and opening his door.

 

“That's a good place for it,” Scott said, also opening his door and getting out.

 

“Wait, I'm stuck in here...and there's no ice cream anywhere,” Isaac whined, falling over across the now empty back seat. Stiles grabbed his legs as Scott simultaneously grabbed his arms, each pulling in a different direction. Isaac chuckled. “This isn't going to work.”

 

Eventually they got inside and collapsed in a heap on the couch, Scott mostly sitting on Stiles' lap and Isaac sprawling out in the other direction on the remaining two thirds.

 

“I thought the couch was bligger,” Stiles remarked as he slid his hands under the front of Scott's shirt and started rubbing his abs.

 

Scott flinched and grabbed Stiles' hands through the material, holding them still. “Stiles! Cold fingers.”

 

“I know, I'm warming them,” Stiles answered with a giggle.

 

“See how you like it,” Scott said with a devious grin before turning and grabbing for Stiles' stomach. The angle and his squirming made it impossible for Scott to get his hands under the front of Stiles' shirt so he settled for getting one hand on his hip and the other inside the back of his shirt.

 

“I do uh...actually like it,” Stiles admitted, pressing his body back against the points of contact and staring intently at Scott's mouth.

 

Scott rolled his eyes but didn't move. Instead he leaned forward and pressed his forehead against Stiles'. He always got affectionate when he drank, and now that Stiles' hands had warmed up, he was enjoying the contact.

 

Isaac laughed from the foot of the couch. “You guys look like you're gonna make out.”

 

Stiles turned and smirked at him. “Maybe we will. We have before.”

 

Isaac folded his arms and scowled at them. He had heard the stories and it reminded him that Scott and Stiles had a special bond that he could never be a part of, that they'd had almost a decade of friendship together before he'd even met them.

 

“Are you feeling grossed out or left out?” Scott asked, letting go of Stiles' neck so he could rub Isaac's leg.

 

“The second one,” Isaac mumbled quietly, looking away.

 

“Awww, Isaac!” Scott released Stiles and crawled along the couch until he was on top of Isaac's mostly recumbent body. “Do you wanna make out?”

 

Isaac looked up into Scott's face, trying to decide if he wanted to or not. He did sort of like the warm pressure of Scott's body pressed against his own and the thought of kissing Scott didn't seem intimidating or unpleasant, just a little weird and confusing. “I don't know. I'm kinda drunk. Can we have ice cream first, then decide?” he asked.

 

Scott grinned down at him and kissed his forehead instead of his mouth. “Good idea. Give us a chance to sober up.”

 

Stiles inwardly groaned. For a second there he thought his desire to see Scott and Isaac sucking face had been about to come true. It hadn't happened, but he decided to focus on the positive: Scott seemed receptive and Isaac hadn't said no.

 

They ate their ice cream on the couch and caught up on a couple of TV shows they'd DVR-d earlier in the week, sobering up in the process. When the second episode ended Scott announced that he was going to take a shower and go to bed.

 

“But what about kissing?” Stiles complained, giving Scott his best pouty face.

 

“Good night!” Scott said with a chuckle as he kissed Stiles on the cheek. “And don't feel left out, dude,” he teased, placing a second kiss on Isaac's cheek.

 

Isaac laughed and gave Scott a brief one-armed hug, but Stiles just frowned at him.

 

“Don't be mad, Stiles,” Isaac said, bumping his leg against Stiles' after Scott had left and they were alone on the couch.

 

“I'm not mad. I'm just disappointed...and kinda horny.”

 

Isaac hesitated, wanting to be sure he wasn't going to regret his suggestion. When he was sure he'd be okay with however this played out he said, “We can make out a little if you want.”

 

Stiles gasped and paused the show they were watching. “Seriously?!”  
  


“Yeah...I mean, if you want to.”

 

Stiles scoffed. “If I want to? Dude, you're hot as fuck _and_ one of my all time favorite people. Of course I want to.”

 

Stiles put his arm around Isaac's back and pressed himself against Isaac's body as he leaned in for a kiss. Isaac had already closed his eyes when Stiles stopped, his lips poised over Isaac's. “Wait, you're sober enough to consent right? I'm not taking advantage of you or anything am I?”

 

Isaac reopened his eyes. He was startled to find Stiles so close but didn't move back. “No, I'm fine now. I barely feel tipsy anymore. Besides, everyone experiments in college right?”

 

“Well, that's the glorious rumor I've been waiting to substantiate,” Stiles said with a shrug before closing the small space between them and sealing his mouth over Isaac's.

 

Isaac gasped and froze for a second, unsure what to do. Then he decided if he was going to experiment, he was going to do it right. Besides, it was kind of cool that he and Stiles were doing this and he didn't want to seem like a bad kisser, so he raised his hand to the back of Stiles' head and pulled him closer, simultaneously parting his lips and flicking his tongue over Stiles' lips, inviting him to take things up a notch if he wanted.

 

Stiles moaned into Isaac's mouth and tilted his head, deepening the kiss and pressing his tongue against Isaac's, and _holy fuck his tongue was in Isaac's mouth!_ Isaac's gorgeous, sexy mouth – and wow, now he tasted like vanilla and Isaac, and Stiles was definitely still a huge fan of both.

 

Isaac didn't know what to do next. Stiles was moaning and trembling lightly against him, obviously way more into this than Isaac was. However, Isaac didn't want to stop and he wanted to give Stiles some encouragement so he grabbed Stiles' hand and pulled it into his lap. He wasn't hard, but he thought Stiles might enjoy feeling him up anyway.

 

Stiles broke the kiss in surprise, licking the roof of Isaac's mouth as he pulled away – and god he was going to burn that sensation into his brain. “Seriously? You're okay with this?” Stiles asked, gently rubbing Isaac's balls, _his fucking balls_ , through his pants.

 

Isaac nodded. “Sure, I want you to have fun.”

 

“Are you having fun?” Stiles asked, tone serious, because as much as he really wanted to keep going, there was no way he was going to let anything happen that Isaac might regret later.

 

“Yeah,” Isaac decided, asking himself that same question. “Being kissed and having my crotch rubbed isn't exactly terrible.”

 

Stiles licked his lips and tried to stay calm. “I-I could do better if you took your pants off.”

 

Isaac pressed his lips against Stiles' in a brief kiss before pushing him back enough so that he could stand. “That makes sense.”

 

Stiles' eyes widened in awe as Isaac unbuttoned his jeans and slid them off, revealing a pair of loose, but sleek, blue boxer briefs – and okay technically seeing Isaac lounging on the couch in his underwear wasn't exactly unprecedented, but the current context made tonight easily a hundred times sexier. “Thank you,” he breathed with absolute appreciation.

 

Isaac laughed as he sat back down sideways on the couch, one leg tucked under him and the other hanging off the edge, his knee between Stiles'. Isaac grinned at him. “Wow, I've never once gotten a 'thank you' for taking my pants off before.”

 

“Then you've been taking your pants off around idiots,” Stiles told him.

 

“I've definitely taken my pants off around you before,” Isaac pointed out.

 

“I rest my case,” Stiles said, fisting the front of Isaac's shirt and yanking him back into the kiss. His heart was pounding in his chest as he tentatively reached into Isaac's lap with his other hand and started carefully messaging his soft, but hefty bulge.

 

Isaac moaned into Stiles' mouth as he felt himself swelling in Stiles' hand. It felt really good and there was something very exciting about doing this with Stiles. There was just one thing worrying Isaac. “This won't mess things up will it?” Isaac asked, breaking the kiss.

 

Stiles shrugged and stared lasciviously at the tent in Isaac's lap as he continued stroking it through the soft, thin cotton fabric. “It won't mess anything up as long as you take your underwear off first.”

 

“What?”

 

“Yeah, it's fine. I'll catch it...or swallow it.” Stiles winked at him. “I swallow by the way.”

 

“I meant mess things up between us,” Isaac clarified, trying to stay focused as Stiles' finger rubbed circles over the tip of his cock through his underwear.

 

“And by _between us_ you don't mean the couch cushion?”

 

“Stiles,” Isaac intoned in his best long-suffering voice. It was undermined a bit by the pleasured undertones thanks to the slow handjob Stiles was still giving him.

 

Stiles reluctantly stopped jerking Isaac off through his underwear and made eye contact. “I don't think it will. When me and Scott messed around it made us closer. But if you don't think you'll feel good about this later, you're right. We need to stop.”

 

“I–I don't want to stop. I just...you and Scott got _closer_?”

 

Stiles smiled fondly. “Yep.”

 

“Well...getting off and bonding even more in the process does sound like a pretty good deal.” Isaac nodded, making his final decision. “Okay, take off your pants.”

 

“Oh dude, no that's okay. You don't have to do anything to me, or even see me do anything to myself. Let's just focus on you and I'll handle myself later.”

 

Isaac frowned and pushed Stiles' hand away as he reached for Isaac's lap. “I get that you're trying to be cool and make me comfortable, but frankly it's kind of offensive that you think I'd be that selfish, with anyone, but especially with you.” Isaac cupped the side of Stiles' face and placed a chaste kiss on his lips. “If you're getting me off, I'm getting you off, and obviously this'll be my first time handling another guy's equipment, so by all means, give me pointers as we go.”

 

“You are so awesome!” Stiles declared, giving Isaac a hug then a quick, sloppy kiss on the mouth, too eager to get out of his pants to be precise. “Boxers too or...?” Isaac nodded so Stiles hooked his thumb into both his pants and his underwear and slid them briskly down his legs. Unfortunately his feet got caught in the cuffs and the next thing he knew he'd toppled over backwards onto the couch, landing hard against the side of Isaac's body.

 

Isaac laughed and shoved playfully at Stiles. That had actually been perfect and had gone a long way toward diffusing some of Isaac's anxiety. This was Stiles, his klutzy adoptive brother and best friend (along with Scott). They could fuck each other's brains out and nothing would ever ruin that bond. It probably would make them closer.

 

“Here, let me,” Isaac said, getting off the couch and grabbing one of Stiles' flailing legs. Once he had freed it from Stiles' pants, he grabbed Stiles' other leg and repeated the process.

 

Stiles sat still on the couch, legs spread so that Isaac could see everything, but not touching himself or doing anything that might make Isaac uncomfortable.

 

Isaac took him in slowly, resisting the instinct to look away. Isaac had seen Stiles and Scott naked lots of times, such as when they were changing for lacrosse, going swimming, or coming out of a shower. He had even seen them erect on numerous occasions when he had accidentally walked in on masturbation sessions or once when he came home early and found Scott having sex with his ex-girlfriend, Allison, on this very couch. However, all those other times he had just seen flashes of their equipment; it had always either been accidental or at least incidental. He had certainly never stopped and examined things before. Yet that's just what he was doing now and it was oddly exciting.

 

Isaac wasn't a dick expert, but he judged Stiles' to be about average in length, maybe slightly longer. He estimated it was about six-and-a-half to seven inches. It seemed a little bit less girthy than average but not significantly. It fit him well actually: longish and slightly slim, just like Stiles himself. He kept his pubes short and neatly trimmed and his balls shaved smooth, which Isaac had already known anyway from their basically boundary-less conversations. Stiles had low hanging balls, which Isaac had also known from conversation, just as he knew Stiles loved having those balls played with.

 

“Is this okay?” Stiles asked, glancing down at his erection self consciously. “I honestly don't mind putting my underwear back on if you want me to.”

 

“Stop being an idiot,” Isaac said as he rejoined Stiles on the couch and then leaned in for a kiss. As Isaac's tongue slid into Stiles' mouth his hand reached between Stiles' legs. He gently but firmly took hold of his nuts and began carefully rolling them around in his palm. They were hard yet pliant and _very_ warm. Holding them gave Isaac an unexpected rush of power, even though he would never do anything Stiles didn't eagerly want.

 

Stiles yelped and thrust his shaft against Isaac's inner wrist. He moaned lewdly into Isaac's mouth and lightly nipped his bottom lip as the delicate rolling became a full-fledged massage. Meanwhile, Stiles' fingers had found their way back to Isaac's clothed dick. He jerked Isaac's shaft with one hand as he used the fingers of his other hand to tickle the underside of Isaac's cockhead.

 

Their bodies were pressed close together, so close that their arms and legs prevented Isaac from getting his other hand into Stiles' lap. He settled for fisting the short hair at the base of Stiles' skull and gently pulling, remembering another kink Stiles had shared over the years.

 

Stiles was panting as he broke the kiss several minutes later, lips tingling blissfully, but not nearly as blissfully as his balls. “Fuck man, you really know what I like.”

 

Isaac laughed and gave Stiles' his biggest grin, remembering that his happy smile was another thing Stiles enjoyed. “You talk about sex _a lot_.”

 

“Will you uhh...” Stiles eyed the wet spots in the front of Isaac's boxer briefs where he had gotten him leaking thanks to prolonged cock teasing.

 

“Oh yeah, of course,” Isaac said before he lay back on the couch and arched his hips, hooking his thumbs into the waistband of his underwear and pulling them down.

 

Stiles licked his lips and swallowed hard. That was definitely a flash of Isaac's taint and asscrack he had just seen before he sat up again, and goddamn was Stiles ever going to try to burn that image into his retina. He was immediately distracted, however, as Isaac's exposed erection came into view.

 

“Holy fuck!” Stiles declared, gaping and staring openly at it.

 

“Wh–what is it?” Isaac asked, feeling self conscious with the way Stiles was looking at him. He didn't think he had anything to be embarrassed about and hoped that had been a good reaction, but either way it was disconcerting.

 

“Isaac, you seriously have the most beautiful cock I've ever seen in my life,” Stiles said, looking away long enough to make eye contact as he said it.

 

“Oh come on, it's not _that_ big,” Isaac said, feeling himself blush from the attention. That's not to say he wasn't enjoying it immensely.

 

“It's not the size, I mean it _is_ a great size – what is it, like eight inches?”

 

“Eight-and-a-half on a good day,” Isaac answered proudly.

 

Stiles nodded. “Yeah, great size, but that's not what I mean. It's just fucking gorgeous. May I?” Stiles asked, desperate to touch it but wanting to make sure he had explicit permission first. When Isaac nodded he didn't waste any time gently wrapping his fingers around it.

 

Isaac moaned softly and bucked against Stiles' hand. It hadn't really been that long since someone had touched his cock – Isaac did pretty well with hookups even though he didn't have a regular girlfriend – but it seemed like an entirety nevertheless.

 

“Wow it even feels perfect. The curvature, the heft, thickness-to-length and cockhead-to-shaft ratios...Seriously man, I think your dick is like mathematically perfect. It's the Platonic Ideal of a cock.” Stiles moved it around slowly and carefully, making sure to examine it from every wonderful angle.

 

“Damn, that's quite a line,” Isaac answered, practically glowing with pride and confidence now.

 

“Not a line,” Stiles insisted, shaking his head. “Perfect, perfect cock. Can I lick it?”

 

Isaac barked out a sharp laugh at the sudden requested. “Go for it.”

 

Stiles moaned in anticipation and slid onto his belly on the couch, his legs hanging off the edge. He pressed his left hand firmly against Isaac's pelvis, enjoying his soft, warm bush. Isaac kept his pubes trimmed like Stiles, but they were longer. It made him seem neat and groomed yet still natural and masculine. His balls were smooth too, but the grooming stopped around the perimeter of his sack, which had thick tufts of light brown hair peeking from the sides. The effect made his balls and cock looked exquisitely nestled, showcased between his thick, muscular thighs, below his lean, sculpted stomach, and against a beautiful light brown backdrop of velvet.

 

Isaac resisted the urge to thrust and buck, or point out that Stiles had just promised him some cock licking. He knew Stiles basically had two modes: unable to focus or hyper-focused. It felt nice seeing that content, excited gleam in his eye as he explored Isaac's manhood. Isaac could be patient if Stiles was enjoying himself this much.

 

Stiles gripped the base of Isaac's shaft with his right hand and leaned in close, nose hovering over Isaac's balls as he enjoyed the raw, crispness of his adopted brother's pheromones. He reminded himself vigorously that Isaac was his _adopted_ brother, that there was nothing wrong with his overwhelming desire to suck Isaac's balls and choke on their heavenly dense, purely sexual aroma.

 

Stiles didn't have permission to suck Isaac's balls, however, and he wasn't sure how he would feel about it. Stiles loved having his own balls sucked, but it was a love it or hate it type of thing, and he wouldn't risk doing something Isaac might hate. Then Stiles remembered that he did have permission to suck something else. His gaze snapped up to Isaac's long, thick shaft and he needily humped the sofa cushion as he raked his eyes along it before zeroing in on Isaac's cockhead. It was swollen and flushed pink, a perfectly proportioned mushroom cap with just the right flare and slope. _Fucking hell! Isaac needs to become a cock model or something._

 

Isaac's cockslit glistened slightly in the light, calling Stiles' attention to a small droplet of precum beading on the tip. Without another thought Stiles plunged his tongue against it, lapping the treat off the end and then immediately wrapping his lips around Isaac's cockhead and vigorously tongue-flicking the sensitive underside.

 

Isaac gasped and gripped Stiles' head. For all of two seconds he struggled to hold still, then he remembered that Stiles _liked_ to have his hair pulled and talked about how hot it was when guys got aggressive with him during a blow job. “If you don't like this please tell me,” Isaac said in a shaky voice before pressing his blunt nails against Stiles' scalp and holding Stiles' head in place as he began thrusting into his mouth.

 

Stiles gagged and swallowed around Isaac's cock, whimpering and moaning as his eyes started watering and his own cock throbbed hard against the cushion. Unfortunately Isaac must have misinterpreted Stiles' reactions because he instantly stilled his hips and let go of Stiles' head. “Mmm Uhnn,” Stiles hummed urgently against Isaac's erection, letting go with one hand and giving Isaac a thumbs up.

 

A wave of relief washed over Isaac. Not only hadn't he crossed a line he was getting the green light to keep going, which he immediately did, pistoning the blissfully hot, wet back of Stiles' throat with an abandon he had never allowed himself before. Stiles kept choking and gagging but also periodically flashing Isaac more thumbs up. A few minutes later, Isaac took off his shirt as he became overheated and Stiles immediately started cascading his hands up and down Isaac's chest and stomach as he deep-throated him. 

 

“Whoa!” Scott exclaimed as he walked down the stairs and found Isaac pumping Stiles' mouth in a way he had only seen in porn before. It wasn't a complete surprise, however, considering he had only gotten out of bed _because_ he had heard sex sounds coming from the living room and eventually decided _fuck it_ he wanted in too. 

 

“Oh my god!” Isaac shouted as he sat up, insistently pushing Stiles away from his crotch.

 

“Hey Scotty,” Stiles croaked with a smile at his other best friend. His throat was sore in the best possible way and while he was definitely a hundred percent sober at this point, he was utterly drunk on lust. “Want a turn in my mouth?”

 

“Fuck yeah!” Scott answered, grinning as he peeled his shirt over his head and threw it on the ground, then stripped out of his pajamas pants. 

“Alright!” Stiles fist pumped the air. Tonight was going so well!

 

“You, uh...what?” Isaac looked back and forth between them as Scott came and stood by the end of the couch. He knew they had blown each other before, but as far as he knew it had been years since it happened and he hadn't expected them to be _this_ casual about it.

 

Scott shrugged and then gasped as Stiles unceremoniously swallowed his dick to the root. “You guys got me really worked up with all that moaning. Wait, you don't mind do you?”

 

Stiles pulled off of Scott's cock with a satisfyingly lewd pop and turned to Isaac. “Wait do you? Did you want this to just be us?”

 

“No?” Isaac answered, trying to make sense of his feelings. His no was automatic – he had always shared everything with Stiles and Scott, of course he didn't want to exclude Scott. Something felt unsettlingly different with Scott here, however.

 

“Aww dude, you're feeling left out again,” Scott said as he recognized the same look on Isaac's face that he had seen earlier in the night when he and Stiles had almost made out.

 

“Oh,” Isaac said as the pieces clicked into place. There was no use denying it so he just nodded.

 

A moment later Stiles had literally thrown himself on top of Isaac and Scott had wrapped his arms around Isaac and was cradling Isaac's face against his stomach. Isaac was surprisingly comfortable with the fact that Scott's wet erection was pressed against his shoulder. All that seemed to matter was the intensity with which they were hugging him and the speed at which they had done it.

 

“You know we don't love each other anymore than we love you, right?” Scott asked, fingers carding through Isaac's hair the way they had on the Uber ride home.

 

“Yeah man, you're our brother. Equally intense love here,” Stiles answered, pulling back enough to look at Isaac then placing a chaste kiss on his lips.

 

Isaac laughed and felt a flush of embarrassment. “Maybe you shouldn't emphasize the brother part right now.”

 

Stiles snickered. Isaac kind of had a point.

 

“Well we are brothers,” Scott insisted. “Just without the genetics to make this creepy. Plus we were older when our families merged so” –Scott shrugged– “it should be fine.”

 

“Okay, I guess you're right. Carry on sucking. I'll...” Isaac trailed off. What _was_ he supposed to do? Watch and jerk off? That wouldn't work; he was getting off on experimenting but he didn't think he would get off on just watching. Should he leave and finish himself off? That seemed unsatisfying. Turn on the TV and kick back while he waited his turn? That would probably distract Stiles.

 

“I have an idea,” Scott said, letting go of the others and turning to leave. “Let's go to my room.”

 

Stiles shucked off his shirt, the last piece of clothing he was wearing, and raced up the stairs after Scott because one, Scott's idea obviously involved sex and was probably going to be awesome and two, Scott's ass. On the stairs. Naked and bouncing. Isaac probably wouldn't be able to properly appreciate that view anyway, so he could bring up the rear. Stiles snickered. Isaac could certainly bring up Stiles' rear if he wanted to. _Good god, I hope he wants to!_

 

Isaac wasn't sure if it was his imagination or not but Stiles seemed to be wiggling his hips more as he climbed the stairs in front of Isaac. Isaac curiously checked out Stiles' ass, trying to figure out if it did anything for him. It was smooth, which Isaac decided was a plus. Isaac had seen a line of black hair peeking out of Scott's crack as he turned to leave and his asscheeks had a smattering of dark hairs growing outward from that central line and upward slightly from the backs of his legs. Stiles on the other hand kept everything really smooth back there, which was what Isaac was used to from his past sexual experiences. Stiles' ass was shaped differently of course, more masculinely, but it was still a nice ass, and Isaac was incredibly horned up by this point from having just received the best blow job of his life but not getting to nut. If Stiles wanted to take their experimentation to the next level and let Isaac fuck him, well Isaac was more than willing. _Fuck, I hope he wants to!_

 

Scott could practically feel Stiles' eyes on his ass as he finished his ascent up the stairs and walked down the hall to his room. He had no doubt that Stiles wanted to fuck him and Scott wanted it just as bad. Scott was completely straight, but he was also completely into prostate stimulation. His ex-girlfriend Allison had used a strap-on on him almost as often as he had fucked her. Since they had broken up Scott had been getting very reacquainted with his dildos and butt plugs during solo play, but there really was no substitute for getting fucked by an actual person. He had almost broken down and asked Stiles to fuck him on more than one occasion over the last few months, but they hadn't messed around since they were horny teenagers and he hadn't been sure how Stiles would react until now. _Damn,_ _is he gonna give it to me good!_

 

 

 

**Notes for the Chapter:**

> This part was basically all just set up. In the second and third parts they'll have lots of very explicit, very loving sex with each other. I'm going for an intense, porn with feelings type vibe. The with feelings part necessitated a longish setup with backstory and characterization, but the next parts will be pretty much all action and dialogue with the three of them just changing from one activity/position to the next.


	2. Lips and Lubricants

 

 

**Everyone Experiments in College**

**Part** **2:** **Lips and Lubricants**

 

“Isaac, you get on the bed,” Scott said, pointing toward the back corner of his bed by the wall. As soon as Isaac was in place he climbed up after him, but sprawled out horizontally next to Isaac's waist. “Now, Stiles, you can sit there” –he pointed to the empty space near the head of the bed next to Isaac– “And you can blow me while I blow Isaac.”

 

“Awesome!” Stiles declared, settling into the open space.

 

“Wait, _you're_ gonna blow me?” Isaac asked, leaning up on his elbows and looking across the bed at Scott. He was staring intently at Isaac's erection and taking deep breathes, obviously trying to psych himself up.

 

“Yeah,” Scott answered, trying not to sound nervous. It had been years since he had sucked a cock and Stiles was the only guy he'd ever done it with, but that was sort of the point: it was time to do this for Isaac.

 

Isaac felt a tingle of excitement and happiness, both in anticipation of his blow job and also because he knew exactly what Scott was doing. He was going out of his way to make Isaac feel included. It was the same thing he had done countless times when Isaac had first started living with them. It hadn't been necessary very often recently, but it felt good knowing nothing had changed. Scott was always going to look out for his feelings. Isaac didn't even feel needy or uncomfortable about it because he had seen Scott do the same thing for Stiles just as often over the years. It was just who Scott was.

 

“Wait,” Isaac said, stopping Scott just as his fingers wrapped around Isaac's shaft. Scott let go quickly like he had done something wrong, but before he could say anything Isaac was already beaming at him and sitting up. He pressed their partially open lips together and gently sucked Scott's bottom one into his mouth for just a second before pulling away, ending his first kiss with Scott before either of them had a chance to get too into their heads about it. “Thank you,” Isaac said quietly, then lay back down.

 

“Fuck, that was so hot,” Stiles said, stroking his cock and looking back and forth between Isaac and Scott. “I know that wasn't about me at all, but I'm going to say thanks too.”

 

Isaac rolled his eyes and Scott grinned at them both, legitimately appreciating both Isaac's affection, which was always nice, and Stiles' sexual attention, which he hoped to parlay into getting his ass fucked.

 

Stiles watched with rapt attention as Scott tentatively licked the head of Isaac's cock, then started jerking off the base of his long shaft while he sealed his lips over the top quarter and began making slurping noises. _Fuck! And I thought it was hot watching them kiss._

 

Stiles stroked himself and enjoyed the show for a few seconds before remembering that he had a job to do, a really fun job. He gripped Scott's inner thighs, relishing the sensation of soft curly hairs, hot taut skin, and strong fleshy muscles, as he hunched over on his knees and enjoyed an up-close view of Scott's equipment. Stiles moaned low in his throat. Isaac's cock was gorgeous, elegant, but Scott's cock was all business, primal. It had grown since the last time Stiles had sucked it, filled out just like the rest of Scott. Stiles estimated it to fall somewhere between his own and Isaac's in length, but it was a thick, girthy monster, already swathed in prominent veins that Stiles knew would bulge beautifully once he got Scott worked up. It was wider and flatter than it was deep and it had a significant up curve. It was a shame that Scott never fucked guys with it because it was a cock just made to pound someone's prostate. Getting it in would be a challenge, but Stiles liked a challenge.

 

When they were younger and trading BJs on a semi-regular basis, Stiles had made Scott shave so that he wouldn't get pubes in his mouth. It was a practice Scott had clearly discontinued in the intervening years, yet Stiles found himself not minding. Scott's dense black thatch and slightly fuzzy sack worked perfectly with his thick, powerful dick and big, heavy balls. Desire pooled in the pit of Stiles' stomach: he needed this cock inside him. 

 

For now Stiles would settle for having it inside his mouth. He gently cupped Scott's balls, enjoying their weight but vowing to drain them. He placed a kiss on the mouth of Scott's meaty cockhead and slid down to the hilt, ignoring the way it made him gag and drool.

 

A few minutes later, Stiles was deep-throating Scott as he stroked himself, and Scott was trying his best to stay focused on Isaac's dick and avoid scraping him with his teeth. He was pulling out all the tricks he could remember to make this good for Isaac, but he was frustrated by his inability to get more than half Isaac's shaft in his mouth without making himself gag. Meanwhile, Stiles did something un-fucking-real with his tongue and Scott shivered and moaned hard against Isaac's dick. _Dammit, why can't I do_ that _with my tongue for Isaac?_

 

As Isaac lay there getting pleasured by Scott he felt ashamed of himself. Scott wasn't nearly as skilled as Stiles – who was literally the best cocksucker Isaac had ever had (Stiles would love that compliment and Isaac intended to pay it later) – but Scott was obviously doing everything he could to make Isaac feel good. He was even unconsciously stroking a sensitive spot on Isaac's inner thigh with the thumb of his free hand, the one that wasn't actively jacking the base of Isaac's shaft. It felt surprisingly nice physically, but more than that it conveyed Scott's feelings: blowing Isaac wasn't a burden, it was something he was happy to do for him. Isaac needed to man the fuck up and pay it forward.

 

“Stiles, come here,” Isaac said, shifting over on the bed and tugging on one of Stiles' calves.

 

“What's up?” Stiles asked after taking Scott's erection out of his mouth. He took the opportunity to rub it back and forth across his cheeks and lips, both to continue providing Scott with stimulation and also because he was rubbing Scott's cock all over his face and – yeah, he didn't need more of a reason than that.

 

Instead of answering, Isaac pulled Stiles closer to him by his legs. Then with one hand he carefully resumed the ball massage he had started downstairs and began jerking Stiles off for the first time with his other hand.

 

“Uhnn!” Stiles quivered and spread his thighs, making sure Isaac had all the access he needed. “Thanks man. God that feels _really_ good!”

 

Something inside of Isaac awakened as Stiles kept moaning and bucking in his hand. He lowered his face and gently held Stiles' balls in place as he licked them and then rolled them around in his hand with his tongue.

 

Stiles choked on Scott's cock, which he had just re-swallowed, the instant Isaac's tongue touched him. He had thought Isaac was just going to give him a hand job and rub his balls, which would have been more than awesome enough, but now... _Fucking fuck fuuuckkkk!_ Isaac had just sucked Stiles' left nut all the way into his mouth and – yep, if Isaac hadn't already been one of Stiles' favorite people, this would have sealed the deal.

 

Stiles braced his head against Scott's pelvis as Isaac sucked his other ball into his mouth and then began jerking him off with both hands, essentially keeping every part of Stiles' genitals directly stimulated at all times. Stiles was still up to his uvula in Scott's cock but he was momentarily too delirious to do anything but whimper and hold on.

 

Scott noticed the shift in Stiles' behavior and raised his head from Isaac's dick long enough to see what was going on. He grinned when he saw what Isaac was doing and extended a hand to Isaac's chest, squeezing and messaging his right pec and nipple. “Way to go, man!”

 

Isaac basked in their approval and a wave of pride rolled over him. He was having _a lot_ more fun than he had expected. The way Stiles was reacting, grinding his crotch against Isaac's face and hands and gurgling incoherently against Scott's dick, was every bit as satisfying as going down on a girl and making her cum against his face. In fact Isaac found himself kind of hoping Stiles would blow all over him. With that surprisingly enticing thought in mind, Isaac released Stiles' balls from his mouth, instantly replaced his hands to keep Stiles dialed up, and then began licking sloppily up his shaft. He wanted to know what it was like to be a proper cocksucker. As Isaac's tongue flicked over Stiles' slit and he tasted Stiles' juices, he automatically sucked Stiles' cockhead into his mouth; he _wanted_ Stiles' cockhead in his mouth.

 

Scott gave Stiles a few minutes to get himself under control then lifted his face away from Isaac again. “Hey Stiles, can I ask a personal favor?”

 

Stiles pulled off Scott's dick and laughed. “More personal than this?”

 

Scott laughed nervously. “Um, sort of. Will you finger me?”

 

Stiles' eyes flared with lust and images of Scott's ass bouncing up the stairs ahead of him filled his head. “Yeah, I can do that.”

 

“Thanks, man, you're the best,” Scott answered, confident that adding _And now please fuck me_ when Stiles was done would be well received. He really wanted something in his butt when he came and if Stiles did say no – which he would totally respect – he was going to use one of his toys while he unloaded.

 

Isaac felt another thrill of curiosity and excitement as Scott talked about getting fingered. He had already been hoping Stiles would offer to get fucked, but so far he hadn't really expressed any interest one way or the other. He knew Scott liked butt stuff and enjoyed getting pegged by his ex. He wondered if Scott would let Isaac fuck him or if that would be crossing a line Scott wasn't comfortable crossing.

 

Stiles licked up and down Scott's bulging shaft, slobbering all over it and making sure to get his fingers wet. Then he ghosted his tongue delicately over Scott's scrotum, remembering that unlike him, Scott didn't appreciate very much testicular stimulation – or at least he hadn't when they were first experimenting as teenagers. Scott's sack was really just a point of interest along a more particular route anyway. Stiles gently cupped Scott's balls and lifted them out of the way, exposing a swollen taint covered in a thick nest of black hair. Stiles felt another flare of lust and wished he could rub his cock along Scott's taint, but it was currently in Isaac's mouth and – yeah actually on second thought Stiles decided he liked it where it was.

 

Stiles closed his lips around Scott's taint, rubbing it hard with his tongue and sucking. Meanwhile his finger trailed lazily back and forth between the innermost crease of Scott's asscheeks without actually venturing to his hole.

 

Scott collapsed against Isaac's groin, as unable to focus as Stiles had been minutes earlier. “Stiles, please. _Please_.”

 

“You really want something inside you, dontcha Scotty?” Stiles asked, breaking his oral seal around Scott's taint. He was enjoying teasing him, but he still wanted to keep him happy, so he pressed two knuckles against the wet spot and rubbed.

 

“No, I really _need_ something inside me, Stiles,” Scott answered. The boys had been on their sides to facilitate the daisy chain, but now Scott rolled over and got on his hands and knees instead, limiting Stiles' access to his cock, but giving him greater access to his ass, greater access to what Scott needed most from him. “If you don't want to finger me will you get a dildo out of my drawer?”

 

“I'm just teasing, man, of course I want to.” Stiles licked his lips and ran a brisk hand up and down along the inside of Scott's crack, eyeing his asshole for the first time. This was way beyond anything they had ever done as horny teenagers. Scott's hole was a pert, raised pucker, smooth and rosy pink, like a flashing neon sign that said 'fuck me here' in Scott's otherwise tan, hairy asscrack. This time Stiles didn't hesitate to tap the pad of his spit-slicked finger against Scott's hole, rubbing it back and forth and gradually increasing the pressure until he slipped inside. _Holy fuck, he is so hot and tight!_

 

By this point Stiles had disengaged his dick from Isaac's mouth and was standing on his knees, wholly focused on his new task. Isaac likewise placed a hand on Scott's head, stopping him as he was about to resuming blowing Isaac.

 

“Scott, uh...c-can I go see?” Isaac asked, feeling deeply awkward but also curious. Asking to see someone's asshole wasn't something he had ever done before. In the past it had happened naturally with the girls he was dating or not at all, never as part of a formal request.

 

“Yeah, of course, dude,” Scott answered, wiggling his hips and grinding backward against Stiles' finger.

 

As Isaac knee-walked to Stiles' side, Stiles pulled his finger out and leaned back, giving Isaac an unobstructed view.

 

Isaac hadn't really been sure what to expect. He had assumed he wouldn't feel much of anything, or that maybe he'd feel disgusted and need to immediately look away. That didn't happen.

 

Isaac gasped out loud as a primal urge coursed through his body. “Uhn! I wanna fuck that!”

 

“You do?!” Scott and Stiles asked in unison, their heads snapping to Isaac.

 

Isaac covered his mouth with his hand, his cheeks already blazing with embarrassment. He hadn't meant to say that out loud, or to say _anything_ out loud. He was just feeling a little too uninhibited and hadn't been prepared for his own visceral reaction.

 

“Dude, you totally can!” Scott answered, stomach twisting in desire as he eyed Isaac's cock, appreciating how big it was for the first time. Before he had just been sucking Isaac's cock with the sole objective of pleasuring him, but he had been so focused on doing a good job and on the possibility that _Stiles_ might end up fucking him, that he had never even considered the possibility that Isaac might. Stiles was bi; Isaac was straight. He just assumed Isaac would draw the line at full-on sex. On the other hand, Scott wasn't drawing the line at full-on sex, so maybe he shouldn't have been surprised.

 

“I-I can?” Isaac asked. He let himself look back at Scott's spread asscheeks, at his wet, rosy hole – yep, he still wanted to.

 

“I would love that. Like, you'd be doing me a huge favor. It's been so long since the last time Allison fucked me. If I wasn't determined to get over her, I'd have booty called her like a dozen times by now.”

 

“You would be in so much trouble!” Stiles said, angry at the thought of Scott getting back in a broken relationship just for the sake of sex. Without thinking he slapped Scott's left asscheek in playful reproach. The reverberating smack that resulted sent a wave of desire thrumming through all three boys.

 

“What about Stiles? I don't want to” –Isaac laughed and placed a hand on the center of Stiles' back– “jump the line or anything.”

 

Stiles looked at Isaac's face, down at his gorgeous fucking cock, then over at Scott's pink, needy hole.

 

“Stiles can watch,” he said, stroking himself as he pictured Scott and Isaac fucking. “Stiles would actually _really_ enjoy watching.”

 

“Stiles can also take a turn after Isaac's done,” Scott suggested with a wink. He was pretty sure Stiles really would enjoy watching, but he wanted to make sure Stiles didn't feel left out. That and it had been way too long time since Scott had last gotten fucked; he wouldn't mind both his bros tag teaming him.

 

With the logistics decided, Stiles knee-walked forward again and promptly buried his face in Scott's ass. Stiles enjoyed giving blow jobs more than giving rim jobs, but it was still fun and the fact that it was _Scott's_ hole he was tonguing, preparing for _Isaac's_ cock made it the hottest rim job he had ever performed. He reached around Scott's waist and stroked him while he worked

 

“Oh my god, thank you, Stiles!” Scott moaned and pushed back further as he pressed his face against the bed. He hadn't planned to ask for a rim job, but damn was he ever pleased to be getting one.

 

Isaac watched Stiles for a little while, but he couldn't see much from his angle, just Scott's asscheeks, which he was realizing more and more he desperately wanted to feel hugging his cock as he penetrated him. He couldn't believe that he was about to fuck Scott. _Scott._ It wasn't something he had ever even remotely thought about, yet now it seemed like the most wonderful idea in the world. It was going to feel so great physically and it was Scott. _Scott._ Isaac loved Scott so much. Scott (along with Stiles and their parents) had literally restored Isaac's faith in humanity. Everything about Scott was sweet and kind and good, and now that Isaac thought about it, it felt beyond right what they were about to do. 

 

A moment later Isaac noticed Scott's face smashed against the bed, and even though the sounds he was making were anything but uncomfortable, Isaac grabbed a pillow from the top of the bed and stroked Scott's head, encouraging him to ease up so that Isaac could slide the pillow under him.

 

“How does it feel?” Isaac asked curiously once Scott was looking at him.

 

Scott grinned and sighed; the look on his face pretty much said it all.

 

Isaac felt a quivery flutter in his chest as he looked at Scott, and it went straight to his cock as Scott moaned and shut his eyes. Isaac needed to do something; he needed an outlet for all the lust and affection that were bubbling up inside him. When Scott reopened his eyes, Isaac licked his lips and went for it. “Hey, uh, you remember when we were on the couch earlier and you were on top of me and you offered to make out?”

 

Scott grinned and shifted positions, lifting himself higher on his hands and knees. “Get under here, dude.”

 

Stiles grumbled, annoyed that he was being interrupted now that he had hit his stride, full-on tongue fucking Scott in time with the hand job he was giving him. He was slightly less annoyed, however, as he processed what they were saying. Oh, they were going make out. That was worth the momentary interruption. While he waited he opened the top drawer of Scott's nightstand and retrieved a large bottle of lube, grinning as he saw Scott's bountiful collection of sex toys. Scott was one of the most innocent guys Stiles knew, yet also extremely open and sex positive. He somehow made butt plugs and cock rings seem wholesome.

 

Isaac sat down and carefully slid his knees under Scott's torso as he began wiggling lower on his butt. It would have been easier if Scott had just gotten up completely – Stiles had stopped rimming him for now anyway – but it was sort of a cool challenge, and Isaac half-laughed, half-moaned as Scott licked his cock as it went by his face. The kissing and licking continued over Isaac's abs, chest, and throat until eventually Isaac was fully wedged between the bed and Scott's body. He had no space. Even Scott's forehead was pressed against his own. However, as Isaac looked into Scott's soft, expressive brown eyes he didn't feel even slightly claustrophobic. He felt utterly secure and happy.

 

“I love you,” Scott whispered, gazing into Isaac's clear blue eyes, overcome with emotions. Isaac was incredible. He had been through so many horrible things in his past, things that Scott couldn't even really comprehend, yet it hadn't broken him. Here he was, strong, smart, confident, and somehow still completely willing to trust and see the goodness in people. Isaac was Scott's hero.

 

Isaac wrapped his arms around Scott's back and took a moment to relish the gentle pressure of Scott's chest on his own, grounding him against the sudden swell of emotions yet simultaneously flooding him in them. Yet, Isaac wouldn't drown. He was safe with Scott; he had always been safe with Scott. “I love you too,” he whispered against Scott's lips before they were making out, hard and sloppy and much more aggressively than their sweet declarations had portended. 

 

Stiles felt his own chest swelling with joy as he listened to them and when neither boy had the good sense to buck his hips, Stiles rolled his eyes, slicked his hand with a generous coating of lube, and reached between them. He clumsily slicked them up, then pressed Isaac's erection against Scott's while gently pushing down on Scott's backside until he took the hint and started grinding against Isaac. A moment later they were both whimpering adorably and moaning into each other's mouths.

 

“You're welcome, guys. Glad I could be here to show you how frottage works.”

 

Stiles returned his attention to Scott's ass. It was much more difficult to spread him open now that he was moving and thrusting, but eventually on a back thrust as Scott's cheeks parted, Stiles grabbed him and held him in place, re-burying his face against Scott's hole. After a few seconds, Isaac realized what was happening and took over all the pelvic movement, urgently thrusting up against Scott over and over until they were both trembling so hard that Stiles began to worry.

 

“Don't cum yet, guys. Scott'll be ready soon,” Stiles said, abandoning his rim job in favor of lubing Scott up and fingering him in earnest so that he could make good on his promise.

 

Isaac quaked against Scott, every nerve sparking with pleasure, as Scott tongue-fucked his mouth. Why the hell had Isaac ever said he wasn't sure he wanted to do this? This was one of the best times he had ever had with Scott, and they had had some really good times over the years. 

 

After working Scott over with his fingers for several minutes, Stiles returned to Scott's bedside drawer and pulled out a dildo to use on him. Isaac was big and Scott was wholly trusting Stiles to get him ready. Scott was experienced with anal play, but Stiles wouldn't risk letting Scott get hurt.

 

Scott didn't think he was going to be able to hold out as Stiles fucked him with the dildo and Isaac ground against him. He needed to break the kiss and tell them both to slow down, but that would have required pulling his tongue out of Isaac's mouth and that seemed like much too steep a price to pay.

 

Isaac groaned in disappointment as he felt Stiles pulling his hips lower, away from Scott's – and yes, Isaac had been about to shoot, so it was probably good that his hips weren't lined up with Scott's anymore but _fuckkk_ Isaac had been about to shoot against Scott's hips. He yelped into Scott's mouth as Stiles wrapped well-lubed fingers around his shaft. Oh geez, if Stiles jerked him off even a little this would all be over. But then Stiles was guiding his cock along Scott's warm, slippery taint. _Oh fuck, is Stiles gonna put it in for me?!_

 

Isaac and Scott both went completely slack, still lazily making out but otherwise making no movement that Stiles didn't guide. Isaac gasped into Scott's mouth as Scott's very hot, very wet hole kissed the top of his cockhead.

 

Scott finally broke the kiss and leaned back, arching his back and grinding down now that he felt Isaac at his entrance.

 

Stiles bit his lip and jerked himself vigorously with slick fingers, still hot from Scott's ass, as he watched Scott's rim stretch around Isaac's thick shaft and swallow it hungrily until just the last couple of inches of Isaac's erection remained unsheathed, their positions preventing deeper penetration.

 

Isaac breathed hard and gripped Scott's thick, dripping erection with one hand and his hip with the other as he asked, “Are you okay?”

 

“Soooo okay,” Scott answered, closing his eyes and bouncing on Isaac's steel-hard shaft. It hadn't even hit his prostate yet, but just the full hardness of it was perfect.

 

“Good,” Isaac answered, sitting up and wrapping his arms around Scott as he flipped them over.

 

“Ohh, yeah,” Scott said, head falling back against the mattress as he felt Isaac push in the last few inches and grind out, this time right against Scott's sweet spot.

 

Isaac looked down, trying to get his head around the fact that there was a thick, bulging cock and a pair of large, heavy balls between his lover's legs, that his pelvis was pressed against a set of muscular, hairy thighs. It was different, but as Isaac's brain shifted gears and something fell into place, he suddenly liked it; he _really_ liked it.

 

“I'm not gonna last long,” Isaac whimpered, taking a shallow, hesitant thrust.

 

Scott's hand found Isaac's on the bed. He squeezed his fingers gently and looked into his eyes. “Please, don't hold back. Let go and cum as soon as you're ready.”

 

Isaac pulled out until Scott's rim was gently gripping the coronal flair of his cockhead, then he carefully pushed back in with one long, blissfully slow thrust. “I'm pretty much ready now,” Isaac said in a shaky voice, this time pulling out all the way and sitting back on his ankles

 

Scott immediately sat up with him and just as Isaac's fingers wrapped around his shaft to finish himself off, Scott's hand landed over them, stopping him. “No, Isaac,” –he kissed him and held eye contact as he pulled back– “inside please.”

 

Isaac's jaw dropped and his cock throbbed with excitement in their hands. “Ohh. Are you sure? I-I thought Stiles was still going to...”

 

“Hey Stiles, you mind sloppy seconds?” Scott asked, grinning at Stiles over Isaac's shoulder and already confident of the answer.

 

“Fuck no!” Stiles answered, shaking his head vigorously as he got on his knees and moved closer to Scott and Isaac. He rubbed his hand down Isaac's lean, lightly ridged stomach and pulled Scott's and Isaac's hands away from Isaac's dick. Then he whispered into Isaac's ear. “Cum inside him, Isaac. I want him dripping with your jizz when I fuck him. I wanna get it all over my cock.”

 

 _Damn._ Isaac needed to cum – _now!_ He guided Scott back down to the mattress and urgently plunged inside him, trembling as Scott yelped and moaned in his arms in response. Isaac only managed five heavenly, if erratic thrusts before a white hot wave of pleasure slammed into him and he was gripping the tops of Scott's shoulders much harder than he should have been, helplessly trying to grind his already fully encased cock deeper into Scott as he felt the cum spraying out of it.

 

Scott clenched his hole and dug his ankles into Isaac's ass, urging him to keep bucking as he unloaded.

 

“It f-feels _sooo_ g-g-good,” Isaac bit out, cock still pulsing hard as he rode out another wave of pleasure.

 

“There you go,” Scott said, rubbing Isaac's chest and trying to memorize the look on his face, the way it made Scott feel. “Give it all to me, Isaac. I want everything you have.”

 

Isaac whimpered and collapsed against Scott, the side of his head pressed against Scott's as he kept thrusting with trembling hips, milking out every drop possible into his adoptive brother.

 

“That feels so good. Thank you, Isaac,” Scott whispered into his ear, holding him close.

 

“So perfect, Isaac. That was the hottest thing ever,” Stiles whispered into Isaac's other ear before kissing the space right behind it.

 

Isaac nuzzled against Stiles' mouth for a moment then raised his head enough to kiss Scott. Stiles rubbed his back and arms while Isaac stayed pressed tightly against Scott, enjoying gentle, slow kisses and savoring the rush of endorphins and oxytocin surging through his body. He took his time, indulging his need to touch and be touched until at last his hormones leveled off and his dick softened inside of Scott, signaling that it was time to get up and let Scott and Stiles have their turn with each other.

 

Scott would have happily held Isaac all night if that's what he had wanted, but the moment he got up, all Scott could think about was how absurdly horny he still was. He looked up at Stiles hungrily, relishing the needy, aggressive look on his face. His sex with Isaac had been incredible, gentle and blissfully comfortable, a seamless transition – thanks to Stiles – from making out to making love, and Isaac had brought Scott to the height of pleasure and held him there, letting him ease back down the precipice without plunging over it. But that was over now, and now Scott desperately wanted to be _pounded_ back up that cliff and this time thrown over the edge. He was grateful to recognize the same need in Stiles.

 

 

 

 

**Notes for the Chapter:**

> I originally thought I could cram everything into two chapters but...nope, they still have a LOT more sex to have before I close the curtain on this fic. I expect the third chapter to be the last, and also hopefully the hottest one. I know this isn't an ideal stopping point, but on the bright side the third and final part is already about half written and I think it'll be the most satisfying installment. LOL, I know technically this chapter was only 'satisfying' to Isaac, but rest assured they all get lots more satisfaction in the final part.


	3. Cockrings and Cuddles

 

 

**Everyone Experiments in College**

**Part 3: Cockrings and Cuddles**

 

 

Stiles slathered lube all over his cock and took Isaac's place between Scott's thighs. He gripped Scott's knees, raising his hips higher on the bed and taking a moment to enjoy the view. Scott's hole wasn't quite gaping, but it wasn't quite closed either. A thin trail of Isaac's creamy white cum ran from Scott's opening, down his crack, and back into the cleft of his ass. Stiles rubbed his cock back up along that trail, watching as the sticky black hairs along Scott's crack clung to his cockhead, caressing it as Isaac's spunk gathered against the slit of Stiles' dick. As soon as Stiles' tip reached Scott's opening he grabbed Scott's hips and winched him down, impaling him hard and fast.

 

Scott moaned and gasped as he reached for his cock. “Stiles, yes! Yes! Yes!

 

It was a miracle Stiles didn't cum as soon as he felt Isaac's hot load squishing around inside of Scott and coating Stiles' erection. Scott was very pleasantly loose and used. This was the first time Stiles had ever fucked someone who had just been fucked by someone else, and while Stiles prided himself on being a considerate lover who gave his partners plenty of time to adjust, it was undeniably awesome being able to just jackhammer with abandon from the first moment of penetration.

 

Stiles loved Scott as much as he loved absolutely anyone in the world, and he was definitely going to get emotional when he thought about them having sex later – he was probably going to spend the next week following Scott around like a lost puppy and hugging and cuddling him every chance he got – but, Stiles just couldn't bring himself to be sweet and tender the way Isaac and Scott had been. He was way too turned on: he had watched Scott and Isaac fuck, watched Isaac cum; he was fucking Scott with Isaac's cum. He had no choice; he had to take Scott straight to pound town, _now!_

 

Stiles drilled Scott as hard as he could, the balls of his feet scrabbling against the comforter as he sought purchase to keep up his vigorous assault. Stiles also gave in to his urge to talk to dirty.

 

“Fuck, fuck, fuck your hole is wet, Scott! It's so fuckin' wet and sloppy! Goddamnit Isaac, your hot spunk is just fuckin' everywhere!” Stiles pulled out enough to enjoy of the creamy white froth that was coating every inch of his shaft. “Look at it! It's dripping down my balls now. My pubes are soaked. Fuck, I fuckin' love it. Your cum smells so fuckin’ good on my cock, Isaac. Goddamnit, Scott, your ass is such a hot, cummy, used mess!”

 

“Yeah! Fuck yeah, Stiles, fuck my ass!” Scott begged, getting into the dirty talk as he stroked his dick faster. He fisted the comforter with his other hand as his head began to spin from sensory overload. Stiles was hitting all the right places and he was hitting them _hard_. But it still wasn't enough. It could never be enough when it felt this good. “Harder Stiles, harder. Oh god harder please!”

 

Stiles cursed and raked his eyes up and down Scott's body, using it for inspiration to maintain his frenzied pace. Scott was so unbelievably hot sprawled out on the bed, fucked into delirium and begging for more. His sculpted chest was glistening with perspiration and his nipples were hard, brown nubs. One arm was thrown back over his head, revealing the deep, muscular valley of his armpit, shrouded in black hair and dripping with sweat. Scott's bicep and forearm bulged with muscles as he clenched the blanket above his head, his tattoo twitching erotically. His hair was mussed and his eyes were half-lidded and rolled back in his head – and still he pleaded, begged incoherently for Stiles to keep going, babbled about how incredible Stiles was and how much he needed this as he feebly stroked his hefty cock with his other hand, too lost in the fuck to give it the attention it deserved.

 

Stiles wasn't the only one who noticed Scott's ineffectual attempts to masturbate while Stiles railed him. Isaac was lying on the edge of bed watching them with open fascination and trying to make sense of his confusing feelings. Not his emotional feelings, they were pretty clear: he felt happy, safe, wanted, and loved – basically the whole positive spectrum. It was Isaac's sexual feelings he didn't quite understand. Something about Scott and Stiles fucking was just _hot_ and Isaac couldn't figure out why. It didn't matter, though. Scott needed some help and Isaac had already sucked Stiles' dick. It would have just been weird not to suck Scott's too.

 

Scott whimpered as Isaac scooted closer on the bed and gently pulled Scott's hand away from his erection. It wasn't the main show right now – that was definitely his prostate and the way Stiles was hammering it with unspeakable precision, and _fuck_ Stiles was a good top – but Scott was still enjoying playing with his cock and why would Isaac stop that?

 

_Ohhh!_

 

Scott moaned and melted against the bed as Isaac's lips wrapped around his cockhead. He hadn't realized how dry and sore it had become until Isaac wet it and soothed it with his tongue. _Good god,_ Scott's hand had felt like sandpaper compared to Isaac's mouth.

 

“Fuck yeah, suck his cock, Isaac!” Stiles shouted, grabbing Isaac's hair with one wet, sticky hand and pushing him down further on Scott's erection. He rammed Scott harder as he did it, loving how messed up and overwhelmed Scott looked and equally turned on by how pretty Isaac was with a dick in his mouth, like a slutty male angel or something.

 

Isaac gagged and tried to breath through his nose as he was forced to deep throat Scott's thick erection.

 

Scott's stomach lurched as he heard Isaac gagging and realized he'd gone tense against his body. “Whoa, whoa, Stiles, don't be rough with Isaac.” Scott yanked Stiles' hand away and patted Isaac's cheek, urging him to ease off. The fact that it felt incredible having his cockhead lodged in the back of Isaac's throat was irrelevant.

 

“Oh fuck! I'm sorry, man!” Stiles said, realizing what he had done and feeling like a complete asshat. He stilled his hips, pausing his fuck with Scott, and replaced his hand on Isaac's head, but this time he stroked his hair instead of pulling it. “I got carried away. I'm so sorry.”

 

Isaac pulled off Scott's cock and licked the head a couple times before answering. “No, really it's fine. I trust you both. Let's just keep going.”

 

Stiles shot Scott a questioning look. He nodded so Stiles resumed fucking him as Isaac once again blew him.

 

After a few minutes, Scott was panting and whimpering again. Between them, Stiles and Isaac had turned everything from Scott's waist downward into one giant, glorious, throbbing mass of pleasure. It was only the unpredictability of their actions and Scott's sheer determination to enjoy as much as he could for as long as he could that had allowed him to last this long, but he knew it was going to happen at any sublime moment. “Isaac, I need” –Scott gasped and shut his eyes as Isaac flicked his tongue in time with one of Stiles' thrusts– “I _need_ to cum. Is it okay if I...you know, do?”

 

Isaac didn't hesitate, just gave Scott a thumbs up the way Stiles had done with him earlier. Of course it was okay for Scott to cum down his throat; Scott had let Isaac cum in his ass – and _holy shit_ that had felt amazing. Regardless, Isaac kind of _wanted_ Scott to cum in his mouth. Before tonight it wasn't something he'd have thought he'd have been okay with, but now it definitely was.

 

“Wait no,” Stiles said, stopping his assault on Scott's prostate. “You can't cum in Isaac's mouth.”

 

“I don't think he minds,” Scott answered, frowning at Stiles and annoyed that he'd stopped fucking him.

 

Isaac raised his hand with another thumbs up and kept sucking. _Nope, no objections here._

 

“ _I_ mind. I want you to fuck me before you cum,” Stiles answered, trembling as he thought about how much he wanted that, how much he had wanted it all night. “Fucking you is fucking awesome, but I want some cock too.” 

“Oh.”

 

Scott turned it over in his mind a couple of times. Meanwhile, Isaac had stopped sucking him as he awaited Scott's decision. Stiles stayed inside him, the head of his dick still pressed against Scott's happy place, but he made no move, also awaiting Scott's decision. It wasn't that Scott _didn't_ want to fuck. Isaac's mouth felt wonderful, but he knew Stiles' tight ass would feel so much better. It was just that his ass felt amazing right now and he didn't want that to stop. Of course he would fuck Stiles no matter what; it was sort of the least Scott could do at this point, but if only there was a way that he could also- _Ohhh!_

 

“Hey, Isaac, how much do you love me?” Scott asked, giving him his best puppy eyes.

 

Isaac beamed back at him and sat up so that he could squeeze Scott's shoulders. He was still consumed with affection for both his best friends. “Dude, there's pretty much no limit,” he answered truthfully. He turned and gave Stiles a fond look too, making sure he understood the comment applied to both of them.

 

“Enough to fuck me while I fuck Stiles?” Scott asked hopefully.

 

“I like this line of thinking!” Stiles declared, leaning forward, still inside of Scott, and wrapping his arms around Isaac from behind. He rubbed Isaac’s abs and trailed his hands down to his crotch, gauging his hardness. He was soft but firm and full, a lazy semi. Stiles was confident he could coax him back to rigidity given a little bit of time.

 

Isaac stroked Stiles' arm and gently gripped his wrist as Stiles held his equipment. The casual sexual intimacy between them was weird in the best possible way. Going with it, Isaac turned his head and reach backward, pulling Stiles forward over his shoulder for a sloppy but heartfelt kiss.

 

“I have something that'll help,” Scott said, eyeing Isaac's sizable but non-erect genitals. He reluctantly climbed off Stiles dick and went to the edge of his mattress on hands and knees so that he could reach his nightstand.

 

Enjoying the same easy intimacy with Scott, Isaac leaned over and spread his asscheeks while Scott rifled around in his drawer. Isaac gasped and cringed. Scott's ass looked wrecked. His hole gaped and flared slightly. The hair along his crack and on his taint was matted down and gummy with Isaac's cum where it wasn't slicked with lube. Even his tan asscheeks had a raw, pinkish glow.

 

“Fuckin' hot damn, look what we did!” Stiles declared, smacking Isaac's arm proudly. His eyes were wide with lust and his tongue lolled out of his mouth as he pressed his bare hip against Isaac's and nudged him out of the way.

 

“Stiles, look what we did!” Isaac answered in a much different tone, panic rising, as he watched Stiles play with Scott's loose hole. He smacked it with the head of his cock and made a few rounds around the rim with his tip before gripping Scott's hips and sliding back inside.

 

Scott sighed and mewled as he pressed back against Stiles, hands clumsily bracing him against the drawer. _God, Stiles’ cock feels good._

 

“Scott, does it hurt?” Isaac asked, hand rubbing Scott's back.

“ _Hurt?!_ ” Scott looked backward at Isaac incredulously. “Um, as far as you can get from hurt. It tingles and throbs so good. I'll be kinda sore tomorrow, but it's totally worth it.”

 

Stiles shot Isaac an offended look and lightly shoved him. “Come on, man, I wouldn't let Scott get hurt. I want him to do that to me. Getting a long, deep dicking is awesome."

 

“It really is,” Scott agreed, forcing himself to get up and off Stiles' erection before he lost his will power. He consoled himself with the knowledge that Isaac's would soon be back inside him while he got to enjoy fucking Stiles at the same time.

 

“If you say so,” Isaac said with a shrug, relieved that Scott was okay. He quirked an eyebrow at Scott as he turned and held up a long, thin, tubular piece of black rubber. “What's that?”

 

“You are so adorable!” Stiles said, smirking at Isaac's genuine innocence before leaning in to kiss him.

 

Isaac kissed back and wrapped his arms snugly around Stiles’ waist and back, enjoying the way Stiles' naked, sweaty body felt pressed against his own. Isaac tilted his head and deepened the kiss, initiating a full makeout session even though he was pretty sure Stiles had only intended the kiss to be quick and casual. 

 

Stiles moaned low in his throat and clutched Isaac's shoulders and neck, grinding his desperately needy, overstimulated erection against Isaac's now noticeably stiffening equipment. He happily parted his lips and admitted Isaac's tongue into his mouth, loving how into making out Isaac was now. It was in stark contrast to the _receptive_ way Isaac had kissed him on the couch. This time it was clear how much Isaac actively wanted him and it felt incredible.

 

Scott waited patiently for a little while, but when they showed no signs of letting up he coughed and cleared his throat – no reaction. He placed hands on each their shoulders. “Uh guys?”

 

Isaac reluctantly let Stiles go, but chased his lips for one more kiss. “I love you a lot, okay?” Isaac said, chest brimming with affection for Stiles as he patted and stroked Stiles’ arms at the elbows.

 

“I know. I love you too,” Stiles answered, grinning at Isaac and rubbing his chest.

 

Isaac nodded. That was enough for now. Isaac wasn't sure exactly what he needed or wanted from Stiles, but he knew they weren't done yet. Isaac felt deeply satisfied on an emotional level with the way the night had gone between himself and Scott, but he still had a thick longing to express how much Stiles meant to him. This might be the one and only time the three of them expressed their feelings sexually and Isaac couldn't let this opportunity pass without showing Stiles how important and special he was to him.

 

Scott smiled at them. He regretted interrupting their moment now that he realized it had been about more than sex and fun; nevertheless, since he had Isaac's attention he continued. “Anyway, this is a cock ring.”

 

Isaac looked at the strip of rubber and tilted his head. “I thought cock rings were...you know, rings. Round.”

 

“There's a buncha different kinds,” Scott answered, placing it in Isaac's hand and then pointing at the ends. “See, this one snaps into place. It's easier to take it off and on. I thought that'd be better since it's your first time wearing one.” Scott glanced down and his eyes widened. He gave Isaac an impressed nod. “Oh, I guess you don't need this after all.”

 

“No, wait,” Isaac said, pulling his hand away as Scott reached to take the cockring back. “I want to try it.”

 

Scott shrugged. “Okay, but it's harder to put on when you're already hard.”

 

“So now my erection is a problem?” Isaac asked, frowning down at it.

 

“Dude, your erection is definitely not a problem,” Stiles remarked, eyeing it hungrily and considering asking for a change in line up with Isaac fucking him instead of Scott. He changed his mind back a moment later when he glanced at Scott's girthy beast. _Damn, I want them both!_

 

“Yeah, you have a really nice dick, bro,” Scott agreed, once again anticipating what lay in store for him. “It's like something they'd model a big dildo on.”

 

Stiles scoffed and shook his head. “Isaac's cock is way prettier than any dildo.” He bent over and stroked it with both hands, once again appreciating the symmetry and proportions, the size and heft, the slope and curve, the shapely mushroom cap, and perfect slit. “Seriously, this thing is fucking gorgeous.”

 

Scott studied it thoughtfully for a few moments then glanced at his own and Stiles' in turn.

 

Stiles noticed what he was doing and laughed. “I know right? Way to make us feel inadequate, huh Scotty?”

 

Scott chuckled but nodded. He was proud of his cock and he loved how thick it was, but even though he wasn't personally turned on by penises he could admit Isaac's was probably nicer to look at for people who were.

 

Isaac frowned. He liked the compliments but he didn't want Stiles or Scott to feel inadequate and they certainly didn’t have anything to feel inadequate about.

 

“No, you guys have really great...boners,” Isaac finished, deciding it was the least awkward way to say it. Regardless, he truly meant it.

 

Stiles laughed again. “Yeah we do. Yours is just exceptional. Anyway, lets get back to using these guys.”

 

Stiles picked up the lube, squirted some onto his fingers, and began slicking his crack then teasing his hole.

 

“I’ll help you get ready,” Scott offered, guiding Stiles onto his back on the bed.

 

Stiles allowed the repositioning but shook his head. “Nah, it’ll be faster if I do it myself. Why dontcha help Isaac with his cockring?”

 

Scott glanced back at Isaac who was struggling to get the rubber ring closed around his now fully erect penis and sizable balls. He looked one wrong move away from pinching himself between the two ends of the closure, which Scott knew firsthand was _no fun._

 

“Here, you hold your stuff down and I’ll close the band,” Scott suggested, knee walking over to Isaac.

 

Stiles was sprawled out on his back, legs spread wide as he briskly fingered his ass and watched with satisfaction as Scott and Isaac manhandled Isaac’s equipment into the cockring.

 

“Fuck while I get ready,” Stiles requested, two fingers shoved into his hole as he squeezed more lube onto his palm with the other hand and let it dribble down into him. He had to remind himself why it was a bad idea to cut the prep short and just ask Scott to fucking impale him right now. However, he didn’t think he had ever taken a dick as thick as Scott’s and he knew he needed more time to loosen up and get ready.

 

“So bossy,” Scott remarked with a smirk as he turned around on the bed and took the lube from Stiles. He passed it back to Isaac.

 

“You know you like it,” Stiles answered with a laugh, experimentally trying to slip a third finger inside his hole but withdrawing it when he felt too much resistance.

 

“No comment,” Scott answered, grinning playfully and getting on his hands and knees. His butt was raised and pointed straight at Isaac.

 

Isaac moaned and took a deep breath. Scott’s ass was undeniably masculine. He had a perky bubble butt with muscular glutes and strong, thick thighs. His crack was lined with cummy, lube-slicked hair that continued down to his pendulous, weighty balls. Isaac trembled with excitement as he lubed up his very hard erection and eyed Scott’s well-fucked hole. 

 

Isaac edged forward on the bed, grabbed Scott’s hips, and thrust in quick and easy. _Fuck!_ Scott’s ass felt as good as it had the first time, maybe better, Isaac decided as he realized he wasn’t as desperate to cum. He could take his time and _enjoy_ Scott’s ass as much as he wanted, as much as Scott wanted based on the way he was already moaning and grinding back against Isaac.

 

Isaac squeezed Scott’s asscheeks together tight around his cock, sandwiching it as he slid in and out of the wet heat, getting remnants of his own cum all over his cock. Isaac felt a flush of surprise as he realized he was sort of disappointed Stiles hadn’t unloaded in Scott too. It would have been hot fucking Scott’s ass with Stiles’ cum in it. Isaac could absolutely see why Stiles had gotten so turned on by Isaac’s load being there when he had fucked Scott. Were they going to do this long enough for Isaac to spill a second load inside him? 

 

“I’m ready now,” Stiles said, nudging Scott’s arm with his foot so that Scott would look at him.

 

Scott’s eyes flared as he took in Stiles’ open, vulnerable position, spread out on the bed with legs wide open. His slick cock was trailing a smear of clear fluid across his lean stomach – lube, precum, or both, Scott wasn’t sure – and his brown eyes were wide and warm, a happy smile plastered across his face. Scott’s heart fluttered and he didn’t even mind the loss of Isaac’s dick in his ass as he scrambled to position himself between Stiles’ legs and kiss his mouth. 

 

Stiles was his. It didn’t matter that Scott was straight or that they could never be together in a romantic relationship type way, Stiles was _his._ Scott had experienced everything with Stiles for as long as he could remember. Best friend, step-brother, _soulmate,_ – Stiles was all these things to Scott and so much more. It felt like they had been made for each other.

 

“I love you,” Scott whispered against Stiles’ lips as he reached down between them and lined himself up with Stiles’ entrance.

 

“Yeah, yeah, Scotty. You’re such a sap,” Stiles answered, mouth pulling into a smile against Scott’s. He moaned and wrapped his arms around Scott’s neck as Scott gently breached him and slowly slid home. “I love you too,” he whispered into Scott’s ear.

 

Isaac re-penetrated Scott and edged close against him until the fronts of his thighs were pressed tight against the back’s of Scott’s. Then he collapsed onto Scott’s strong, sweaty back, enjoying the extra body contact as Scott rocked and bucked underneath him.

 

“This is so good,” Scott whimpered, lost in pleasure and endorphins as he took over all the actual fucking, sometimes rolling his hips back and impaling himself to the hilt on Isaac’s cock and other times rolling forward and burying himself balls deep in Stiles.

 

“God, your cock is so good. Damn, I like getting fucked,” Stiles said, squeezing Scott close as he also enjoyed the blissed out look on Isaac’s face.

 

“What’s it feel like?” Isaac asked Stiles over Scott’s shoulder as he writhed against Scott’s back.

 

“Oh it’s so good, Isaac,” Stiles moaned, eyes rolling back in his head as Scott hit his prostate again.

 

“So good,” Scott agreed, whimpering into Stiles’ neck. He panted brokenly a moment later. “I’m about to cum.”

 

“Do it Scotty, fill me up,” Stiles whisper-moaned, sliding lower on the bed against Scott and hooking his heels around the backs of Isaac’s legs. He wanted them both as close as possible.

 

Scott thrust forward and ground out hard inside of Stiles then he pleaded for what he needed to send him over the edge. “Fuck me hard, Isaac. Please god, fuck me hard."

 

Isaac did as he was asked, gripping Scott’s shoulder with one hand and his hip with the other as he pounded into him over and over as hard and reckless as he had ever fucked anyone.

 

“Aahh! AGHH!” Scott straight up screamed as Isaac fucked the cum out of him and sent it blasting into Stiles. He came so hard his vision went spotty and his head swam. He trembled and quaked between Isaac and Stiles. They were the only thing holding him together as his cock exploded and his ass spasmed and pulsed with pleasure. It was almost too intense to take and he was grateful that he didn’t have a choice. He might have tried to ease off Isaac’s cock or out of Stiles’ ass if their bodies weren’t pinned against his own, forcing him to endure what felt like the most powerful orgasm he had ever had.

 

“Nobody move,” Scott pleaded, eyes still squeezed shut as his whole body went slack. His heart was racing and his breath was ragged. He needed to get himself back under control and he couldn’t bear the thought of this moment with Stiles and Isaac ending, of losing the sensation of their arms and legs wrapped around him, their hot, slick flesh pressed against his own.

 

“We’re not going anywhere,” Isaac answered, whispering the promise into Scott’s ear and once against collapsing heavily on top of him, covering as much of Scott’s body as he could.

 

Stiles nodded and tilted Scott’s head with his hands until he had lined up their mouths again. “We gotcha, Scotty,” Stiles said against his lips, thumbs stroking Scott’s cheeks. Soon Stiles’ tongue was back in Scott’s mouth.

 

“So good, Scott. You’re amazing. We love you so much,” Isaac said into Scott’s ear, face nuzzled against the side of his head and hands sliding up and down along his arms.

 

Stiles let them stay like that as long as he could stand, until the weight of his brothers bearing down on his chest was too much to take. At last he broke the kiss with Scott and said, “Can you ease up a little, guys?”

 

Isaac pulled Scott sideways and rolled them onto the bed, his still very hard cock slipping out of Scott’s ass in the process. Scott’s semi-hard dick likewise pulled free of Stiles.

 

Scott whimpered at the loss and nestled deeply against Isaac’s chest and in his arms. “Put it back in,” he requested.

 

Isaac chuckled and lifted Scott’s leg enough to slip back inside. He was happy to oblige him. Scott’s not-so-tight heat was pretty much the most pleasant place he could imagine to holster his erection. 

 

“I want to be back inside you too,” Scott whined to Stiles, facing him on the bed.

 

Stiles kissed him as he scooted closer and tangled their legs together, his needy prick pressing against Scott’s softening equipment. “I want that too, Scott, but I think we’ve got a technical problem.”

 

“Stupid soft dick,” Scott muttered, wrapping his arms around Stiles and pulling him close. If he couldn’t get inside him at least he could hold him and continue to enjoy the contact.

 

“Hey now, I love that dick. It’s big and awesome and it just pumped me full of hot, creamy cum. Give it a break,” Stiles answered, consciously clenching his hole to keep Scott’s seed inside him.

 

One of Stiles’ arms was slid under Scott’s head and the other was around both Scott and Isaac’s bodies as he stroked Isaac’s back and pressed himself firmly against Scott’s chest. 

 

Isaac likewise had one arm crossed with Stiles’ around Scott and Stiles, and his other arm sprawled lazily over their heads. He wasn’t sure if it was the cockring or just the situation in general, but his erection showed no signs of dissipating inside Scott even though he had already cum once. If anything he needed more. That reminded him...

 

“You must be really horny,” Isaac remarked to Stiles. Poor guy had fucked and gotten fucked, sucked and been sucked, and spent all evening making out with Isaac and Scott in turn. And _he_ was the one who was bi and supposedly the most into all this.

 

Stiles laughed. “You have no idea. Total hair trigger. If I humped Scott even a little right now I’d blow all over him.”

 

“Go for it,” Scott said, hand sliding down to Stiles ass and pulling him closer.

 

Stiles panted and fought the overwhelming urge to keep going. Instead he pulled his hips back, carefully avoiding contact on his throbbing cock. “Actually I was hoping to maybe do some more stuff and cum that way.”

 

“You mean like maybe fucking someone?” Isaac asked, stomach tightening as he knew with certainty what he was about to suggest.

 

“Yeah, being inside someone while I came would be pretty awesome,” Stiles agreed, looking at Isaac curiously over Scott’s shoulder and desperately hoping he wasn’t imagining where this was going.

 

Scott on the other hand didn’t have a clue. He shrugged and smiled at Stiles. “I’m not horny at all anymore, but I’m really loose, so you can totally just use my hole till you cum.”

 

Stiles swallowed hard. That wasn’t exactly what he had in mind but _dammit_ that offer sounded really good.

 

Isaac hesitated for a moment. That could happen or...

 

“Or if you want a tight hole you could use mine,” Isaac said, staring at Scott’s ear as he suggested it to avoid eye contact with Stiles. “I mean, I’m a virgin back there so...you might like it.”

 

“Seriously?!” Stiles couldn’t keep the grin off his face. Isaac was so awesome!

 

“I want to see what getting fucked is all about,” Isaac said as confidently as he could manage. He was terrified but he was also still horny and Scott and Stiles had been so into it. Plus he was still desperate to connect with Stiles on the most intimate level he could, and Stiles taking his anal virginity seemed like a good way to do that.

 

Scott rolled over enough to look at Isaac. “Dude, you’ll love it! Getting fucked feels so good, and Stiles is incredible at it.” 

 

Isaac nodded, pulled out of Scott, and sat up. “So what do we do?”

 

Stiles squeezed Scott one more time, hoping he had had enough post-orgasm cuddles. Then he sat up enthusiastically and climbed over Scott to get to Isaac. He pressed a quick kiss to his lips and squeezed his shoulders, then said, “Roll over and get on your hands and knees.”

 

Scott moved to the foot of the bed to give them room.

 

 

 

**Notes for the Chapter:**

> LOL, sorry guys, I write really long smut, so yeah...there’s still one more part. I’m hoping to have it posted by New Year’s, but that’s just a tentative timeline. I’m kinda surprised by how unpopular this story is, which – fine I’m just writing it because I want to, but anyway, since no one seems to be holding their breath I’m keeping it at the bottom of my writing priorities list. My other two fics will update sooner.


	4. Happiness and Hormones

**Everyone Experiments in College**

**Part 4: Happiness and Hormones**

Isaac fluffed a pillow, folded his arms around it, and buried his face against it as he spread his knees on the bed, revealing his hole to someone for the first time. He felt a weird mix of vulnerable yet safe, self conscious yet sexy. He smiled against the pillow at Stiles' reaction a moment later.

“Fucking fuck fuck, man! Damn that's a fine ass,” Stiles said, vigorously jerking his cock a few times as he looked at it. He whimpered and squeezed his balls as the act almost sent him over the edge. He could get off all day looking at Isaac’s ass, but he desperately needed to fuck it, not just look at it.

Isaac's ass was round and muscular. Each cheek mounted majestically like a half globe, smooth and hard, spreading gracefully to reveal Isaac's inner treasures. The top of Isaac's asscrack near the base of his back was smooth and supple-looking; however, midway to his hole in the deepest valley of his crack a smattering of light brown hair appeared. The hair growth thickened slightly and spread to the walls of his asscheeks as it reached his hole. The growth then followed the grove of Isaac’s ass down along the sides of his taint, leaving the taint itself with only a dark blond fuzz as the main trails of hair continued around the perimeter of his shaved-smooth balls. The black band of the cockring contrasted strikingly with Isaac’s medium skin tone and highlighted the size and heft of his balls.

Isaac's asshole was the crowning glory, however. It was every bit as perfect and beautiful as Isaac’s cock, a tight, narrow slot with a tract of soft-looking, slightly darker skin around it, hinting at the silky, smooth goodness that lay within. It was a paler, calmer pink than Scott's hole and didn’t look nearly as needy; however, Stiles was resolved to change that.

Stiles knew he needed to get Isaac ready. He needed to lick or finger him, prep Isaac for his cock, but looking at Isaac’s obscenely hot hole, Stiles’ reaction was visceral. Preparations aside, he _had_ to get his cock all over Isaac’s hole and taint and the instinct was too strong to resist another moment. Stiles’ scrambled forwarded on his knees, propping his legs between Isaac’s as he vigorous tapped Isaac’s hole with the tip of his cock, stoked his shaft up and down and back and forth in Isaac’s plush valley as he massaged Isaac’s swollen taint with his thumbs. Stiles slid his fingers under the black band binding Isaac’s cock and balls, making Isaac whimper and moan as Stiles continued exploring Isaac’s innermost external recesses with the sensitive glans of his penis.

_Fuck, fuck, fuuuuck! This is so hot!_

Stiles’ whole body was trembling as he struggled to still his hips, fought the blinding urge to just keep thrusting against Isaac’s crack until he spilled his cum all over the outside of Isaac’s hole. Stiles didn’t want that, or at least he didn’t want that half as much as he wanted the alternative, half as much as he wanted to explore Isaac’s internal recesses.

“I need to fuck you so bad,” Stiles said, a desperate whine in his voice. 

Isaac bucked back against him, ground the grove of his ass slow and hard along the full length of Stiles’ steel-hard prick. Isaac’s breath was ragged and his heart was pounding as he said, “Do it, Stiles, please do it!”

Stiles took a deep breath and in a burst of determination pried his manhood away from Isaac’s ass. He could do this; he could wait just a little bit longer. He backed up and hunched over, then plunged his tongue against Isaac’s opening, lapping at Isaac’s tight, virgin slot as he squeezed and kneaded his asscheeks.

Isaac gasped and whimpered as he pressed back against him. Stiles’ tongue was warm, wet, and _possessive_ against his hole, licking it, sucking it, prodding it, then trailing up and down and back and forth along Isaac's crack, claiming and slicking every part of him. Then it was back to Isaac's hole for more prodding and lapping. It felt unbelievably kinky and intimate, but also just good, _so fucking good._

Scott had gotten a look at Isaac’s hole too. It was definitely a virginal hole and Scott found himself getting anxious. He trusted Stiles not to hurt Isaac, but protecting Isaac was second nature to Scott and he knew Stiles was amped up and beyond ready to go. Scott needed to make sure Isaac was safe, so he scooted off the bed and went to his nightstand. He perused his collection of toys, selecting the smallest butt plug he had, then a couple of medium and medium-to-large dildos, and finally a large dildo that was slightly bigger than Stiles. He put them all on the bed next to Stiles with an extra bottle of lube just in case. 

Stiles took his mouth away from Isaac’s hole and snickered as he looked at the toys Scott had spread out. “It’s so obvious you were a boyscout when we were little, Scotty. You really take always being prepared to the next level.”

Scott sniggered and rolled his eyes before climbing back on the bed, this time sitting next to Isaac and massaging his shoulders. “You doing okay? You know you don’t have to do this if you don’t want to.”

Stiles’ heart sank at the suggestion, but he didn’t hesitate to add his agreement. His voice was muffled, his face once again pressed against Isaac’s ass. “Oou reary ron’t, ran.” He pulled back, needing to make sure Isaac understood. “You really don’t, man. I don’t wanna do this unless you’re completely sure it’s what you want.”

Isaac laughed and leaned into Scott as he simultaneously pushed back against the pad of the finger Stiles had just pressed against him. It still hadn’t breached him, but he was tingling beneath it. “I’m sure. You both make it seem like getting fucked is incredible.”

“It is!” Scott and Stiles agreed in unison.

“Then I want some too,” Isaac answered, sure of his decision.

“It’s not going to hurt at all, I promise. I’m going to do this right.” Stiles squirted an ample amount of lube into his hand, took a moment to let it warm, then began slicking up Isaac’s hole and his own finger. 

Isaac hissed, momentarily overwhelmed as Stiles’ digit finally penetrated him. It wasn’t physically overwhelming or unpleasant, just a lot to get his head around. Stiles was inside of him, but soon _Stiles_ would be inside of him. Soon Stiles would _let go_ inside of him. Isaac was positive it was what he wanted, but he was nevertheless quivery with nerves and excitement.

“Come here,” Scott said, hand on the back of Isaac’s head as he gently massaged his scalp and the base of his skull. With his other hand Scott repositioned the pillow, gently easing it out from under Isaac’s head and into his lap. 

God, Isaac loved Scott so much in that moment, loved him for being so perfectly attentive and wonderful. Isaac hummed in relief as he collapsed into Scott’s lap, letting the tension ease from his shoulders as he wrapped his arms loosely around Scott’s waist and let Scott soothe him. He nuzzled the side of his face against the pillow as Scott caressed his cheek and rubbed his upper back. 

A moment later, however, Stiles’ finger, which had been cautiously easing into Isaac and gently stretching his ring of muscle, finally sank further in and– 

“Aahh!” Isaac gasped and let out a low, deep moan, openly shivering as the sensation shot straight through his gut and directly _inside_ his cock, making it throb and leak between his legs. “Oh f-fu-fuuucckk!”

“Yeah?” Scott asked knowingly, thumb stroking the apple of Isaac’s cheek and fingertips caressing the soft skin under his jaw. He was so happy Isaac was feeling this and that he got to watch him discover those sensations.

Isaac nodded and whimpered again. _Goddamn it feels good!_

“Have you never played with your prostate before, Isaac?” Stiles asked, gently rubbing circles over the hot, pliant bundle of nerves. The sounds he was eliciting from Isaac made it hard to focus and – _Fuck!_ Isaac sounded so good moaning like that, Stiles was worried just the sounds Isaac was making would get him off.

“No, I’ve never had anything in there before,” Isaac answered brokenly, burrowing closer to Scott’s stomach and tightening his arms around Scott’s waist as he hung on for dear life. The tip of Isaac’s nose was now pressed against the fuzzy hairs of Scott’s treasure trail. 

“I am so getting you an Aneros for Christmas,” Scott told him.

“I am so gonna use it,” Isaac answered, unsure what it even was, but if it was something that would mimic the feeling of Stiles’ finger, then yeah, he _really_ wanted one. 

Lost in lust, Isaac tilted his chin and began mouthing at the long, thin hairs of Scott’s lower abdomen, then swirling his tongue up over Scott’s taut, shallow navel. When he realized what he was doing, he pulled his face away enough to say, “I dunno why I’m doing this.”

Scott massaged his temple. “Don’t over-think it, bro. Just keep doing it if you’re having fun.”

Isaac sighed and began lapping at the deep groves and hard bundles of muscles that formed Scott’s lower abs. _Yep, definitely fun._

By now, Stiles had graduated to fucking Isaac with the small butt plug, but he was starting to feel jealous. His cock was still throbbing with need and he didn’t dare touch it, yet he need _some_ sexual stimulation. His ass was still tingling from Scott fucking him. He was still wet with Scott’s seed and it was slowly dribbling out of his hole and down his taint and balls as he hunched over on the bed, his own ass in the air as he worked Isaac over. He didn’t want to lose anymore of Scott’s cum and there was a simple way to kill two birds with one stone.

“Hey Scott, can you get another butt plug? For me,” Stiles added, wanting to be sure Scott didn’t pull out another starter model thinking it was for Isaac.

Scott chuckled and gently eased Isaac away from his lap, moving the pillow as he leaned over the side of his bed and rifled through his nightstand for a toy that would suit Stiles’ needs. When he found one he tossed it to Stiles; however, before he could close the drawer Isaac also had a request.

“Maybe another cockring too?” Isaac said on hands and knees as he eyed Scott’s re-exposed genitals. Scott’s penis was soft, but it hung long and _thick_ over his hefty balls, nestled erotically beneath his thick, bushy black pubes and the tuft of black hair peeking out from beneath his balls. Desire pooled even heavier in Isaac’s gut. He had seen Scott’s soft dick countless times over the years, but – _Geez! Had it really always looked this good?_

“You wanna put on another cockring?” Scott asked, tilting his head in confusion.

Stiles was confused too. He reached between Isaac’s spread thighs and rubbed his sloppy, slick palm all over Isaac’s completely rigid erection. Thanks to the cockring Isaac already had on, Stiles could even feel veins bulging on Isaac’s shaft – which _fuck!_ Stiles couldn’t wait till Isaac rolled over so he could see all that bulging too. Damn, it was going to be fun fucking Isaac while he looked down and jerked that veiny beast.

Without preamble Stiles sat back on his ankles and rammed the butt plug Scott had just given him into his ass unlubed. Stiles’ ass was still plenty slick with Scott’s cum and the original round of lube, and the sudden ache and throb caused by the rough intrusion were very welcome just then, helping to take the edge off Stiles’ intense need to cum while simultaneously satisfying some of his lust.

Isaac and Scott both looked at Stiles with concern as he yelped, but he just gave them a grinning nod and a thumbs up in response.

“I want _you_ to put on a cockring,” Isaac said, turning back to Scott. “I want to blow you some more. Your junk just looks” –Isaac bit his lip, openly staring– “so fucking amazing right now.”

“Thanks man!” Scott said as he pulled his favorite cockring from his drawer.

“Wait, you don’t mind do you?” Isaac asked, realizing that _oh yeah,_ Scott also had a say in this.

Scott sighed dramatically. “Well, I guess I’ll just have to suffer through another awesome blowjob if it makes you happy.”

Isaac watched Scott put on his cockring with as much focused attention as he could manage now that Stiles had progressed to fucking him with a medium-sized dildo. The new cockring actually was a solid ring unlike the one Isaac was wearing that clasped together. Scott slid first one testicle into it, followed by the other, and then folded the end of his dick down, working it through the ring too. _Wow, I’m really enjoying watching Scott touch himself._

Isaac gave Scott a needy look, which Scott readily understood. He reclaimed his spot at the head of the bed above Isaac, but this time didn’t put the pillow back so that Isaac could rub his face all over Scott’s rapidly swelling cock and pleasantly sensitive balls.

Once Scott was fully hard, Isaac swallowed as much of his shaft as he could take, ignoring the light gagging sensation as Scott petted the back of his head and told him how good it felt. Isaac agreed; there was something deeply satisfying about sucking Scott’s cock while Stiles’ fucked him, more vigorously now, with one of the bigger dildos. 

Stiles took a shaky breath as he pulled out the second largest dildo Scott had given him from Isaac’s hole, which wasn’t a tight slot anymore. It was a beautifully puffy, glisteningly wet oval with rosy pink skin teasing the perimeter of a small dark opening. Fuck, it was hard for Stiles not to objectify it completely, not to rise up on his knees and shove his cock into it then and there.

_It’s not just a fuck hole. It’s Isaac’s fuck hole. Isaac. You love Isaac. You would never risk hurting Isaac. Calm down. Clam down._

Stiles picked up the final dildo, slightly thicker than his own girth. He lubed it generously and very gently eased it inside Isaac, watching in awe as Isaac’s pinkish, fleshy muscle stretched around it, gripping it obscenely. He rocked it back and forth in a tight circle, focusing on easing the resistance. When Stiles was confident that Isaac would be able to take his cock without pain, even if Stiles’ thrusts were clumsy and erratic – because let’s face it, they were going to be at this point – he pulled the dildo back out, slathered more lube all over his fingers, and ran them around the pillowy, hot opening one more time.

_Holy fuck, can my fingers have an orgasm?!_

“Isaac, I-I think we’re ready to go. Turnover please.”

Isaac’s throat tightened around Scott’s cock. He tried to sort out his feelings as he slurped on Scott’s erection one more time before pulling off and repositioning as Stiles had requested. _Fear?_ Nope, not even a little. He felt ridiculously safe and at ease. _Excitement?_ Hell yeah, so much excitement! He desperately wanted this. But also...

Isaac sighed and smiled, chest brimming with emotion as he look at Stiles, who was rubbing his thigh and grinning at him with unbridled enthusiasm, brown eyes sparkling and happy. Isaac usually loved Stiles in a comfortable, familiar way, a deep, quiet bond underpinning their day-to-day interactions, not tonight though; tonight Isaac loved Stiles in an intense, fluttery, oh-my-god-I-can’t-believe-how-awesome-he-is! kind of way.

Isaac sat up and grabbed Stiles’ wrists, gently pulling him forward until he could wrap him up in a hug, not minding at all when Stiles lost his balance and fell on top of him. He nuzzled his head against Stiles’ then turned it and peppered Stiles’ jaw and cheek with kisses.

Stiles giggled and held his face still, reveling under Isaac’s affection. His hands stroked up and down Isaac’s back before they trailed along the back of his neck and onto the sides of his face. He stared into Isaac’s bright, unguarded blue eyes. “Yeah, this means pretty much everything to me.” He looked over Isaac’s shoulder at Scott. “You guys mean pretty much everything to me. Just so you know, this is the best night of my life.”

Isaac surged forward, closing the small distance between their mouths as he captured Stiles’ lips in a kiss. 

A second later, Scott had pressed himself against Isaac’s back and was clutching desperately at Stiles’ shoulders.

When the embrace ended, Scott passed Stiles both pillows from the head of the bed. “Put these under Isaac’s hips.” 

Scott spread his legs around Isaac and eased him backward until Isaac was reclining against his chest and Scott’s chin was hooked over his shoulder. His arms were wrapped snuggly around Isaac’s torso, thumbs massaging his pecs and abs.

Stiles heart raced as he eyed Isaac’s spread open hole, flared and ready between taut, muscular thighs lined with a sparse dusting of brown hairs. Stiles could barely stand it as his gaze flicked up to Isaac’s cock and balls, flushed a deep rosy pink and bulging beautifully. Isaac’s engorged cockhead was darker than before thanks to the cockring. It was a needy purply pink and it glistened with precum. 

Isaac took Stiles’ hand by the wrist and placed on his equipment, encouraging Stiles to rub and fondle to his heart’s content. 

“Thank you,” Stiles breathed more than said, palm slick with Isaac’s juices as he polished his knob.

“Thank _you._ ” Isaac whimpered and moaned, lacing his fingers together with Scott’s on his chest and stomach and snuggling back against him as fierce jolts of pleasure sparked through his body. God Isaac’s life was awesome, held lovingly in one best friend and adoptive brother’s embrace while the other lavished him with erotic attention.

“Do you want me to wear a condom?” Stiles asked, pulling his hand away and rubbing Isaac’s precum on his own cockhead before also slicking up with more lube. “I’m prolly gonna cum in like two seconds when we start, so I don’t think there’ll be time to pull out.”

“Don’t pull out and don’t wear a condom. Just–” Isaac gasped overcome with a heady cocktail of love and lust as he looked up at Stiles. “Uhnn, Stiles, I want you so much. Fill me up, with your cock, with your cum, everything.”

Stiles trembled as he lined himself up with Isaac’s hole, easing forward until Isaac’s hot, wet ring of plush muscle connected with the over-sensitized tip of his dick.

“Ohh FUUUCK!” Stiles eyes widened as he felt his balls drawing up in his sack and his cock quaked with even more tingly energy. Stiles was wrong – two seconds had been a generous estimate. He was cumming _now_ and he had literally just given Isaac the tip. 

“I can’t– it’s, it’s now! it’s _NOW!_ ” Stiles grabbed Isaac’s hips and winched him down onto his cock as he simultaneously lurched forward, slamming into Isaac and bottoming out as he was swallowed up in a full-body orgasm. “Ohh, Uhhn, UHNN!”

Stiles closed his eyes and collapsed against Isaac. He wanted to keep thrusting but it was too intense. It felt like his whole body had been turned into a giant throbbing nerve. Stiles couldn’t breathe and his heart was pounding so hard Isaac must have felt it against his chest. With his last remaining breath, Stiles panted, “It’s so good! It’s _s-sooo_ g-goodd!” 

“Keep cumming, Stiles! Keep cumming!” Isaac urged, legs wrapped tightly around Stiles’ waist, and hand palming the small of his back. “Unload as much as you can.”

Stiles whimpered and did as he was told, flexing his pelvic muscles and trying to make his last few shots harder and fuller as he sprayed Isaac’s inner walls.

It wasn’t until several minutes later when Stiles had finally regained his senses and tried to sit up that he even realized Isaac’s and Scott’s arms were both wrapped around his back and his head was cradled between theirs on Isaac’s shoulder. They were whispering sweet words to him that made his chest swell and had him deciding to stay put for a few more minutes after all.

“That was so good,” Isaac said when at last Stiles had pulled back and sat up, though he was still buried to the hilt inside Isaac.

Stiles laughed and he felt his already hot, sweaty cheeks getting warmer. “Yeah, I’m sure that one whole thrust I managed was awesome for you.”

Isaac cleared his throat and gave his waist a pointed look. His cockhead and shaft, along with the back of Scott’s hand where it was pressed against Isaac’s abdomen, glistened in the light, soaked with his precum. “I almost came. As soon as I felt you filling me I...” Isaac trembled and sighed, then rubbed Stiles’ shoulders. “It was perfect.”

It felt amazing hearing how into it Isaac was and how much he wanted Stiles, but Stiles couldn’t help looking at Isaac’s wet, throbbing cock and feeling disappointed in himself. “Man, if I coulda just lasted longer though.”

“Dude!” Scott shoved at his shoulder. “You lasted longer than either of us. You’ve been having sex all night.”

“And uh...if you want” –Isaac raised his eyebrows and shrugged, a grin lighting his face– “I’m certainly not asking you to stop now.” 

“Oh!” That should have been the obvious solution. Stiles moaned softly as he pulled back and rolled in again, shivering as his cum slicked his erection and squished satisfyingly inside of Isaac.

Isaac sighed contentedly and lay back in Scott’s arm, resisting the urge to touch himself. He wanted to focus on his ass instead, on the needy tingle that made his whole body go slack and the blood rush to his groin.

“You want a cockring too?” Scott offered Stiles.

Stiles scoffed as he ran his eyes up and down Isaac’s sweaty, lean body; his handsome, chiseled features; and his slick, pornographic nether regions. “Have you seen Isaac? I’m definitely not gonna have a problem keeping it up.”

“Yeah, Isaac’s beautiful,” Scott said sweetly, nuzzling his nose against Isaac’s neck.

Isaac giggled and felt himself blushing. He started to protest the compliments but changed his mind, deciding to return them instead. 

“You’re both so hot,” Isaac said, voice straining as Stiles’ gentle thrusts became more aggressive and the needy tingle in Isaac’s ass became a consuming desperation. “I can’t believe how turned on I am. How much I like your bodies.”

Isaac gripped Scott’s bicep, kneading the thick cords of muscle as he writhed backward against his warm, hard chest. Scott was so _strong,_ so _muscular_ and Isaac liked it on a very primal level, on a level that had nothing to do with feeling safe and loved in his brother’s arm and had everything to do with those arms themselves.

Isaac’s eyes tracked over Stiles’ long, lithe torso, paying particular attention to the straining, flexing muscles in his stomach, the graceful sloping planes of his chest, the pert brown nubs of his nipples. Isaac concentrated on the way Stiles’ cock made him feel, not the emotional aspect of connecting with Stiles like this, or even the physical pleasure that came along with the stimulation, but on the _erotic_ thrill itself.

“I’m not straight,” Isaac mumbled to himself as the pieces clicked into place. 

Stiles’ hips jerked and he stuttered to a stop inside Isaac on his next forward thrust. “What?”

“I’m not straight,” Isaac repeated, grinning now as he realized the exciting implications that came with his discovery, the reality that his dating and sex pool had just doubled. “I’m bisexual!”

“Are you sure?” Scott asked, squeezing Isaac closer. “’Cause getting fucked just feels really good. I think most guys open to it would like having their prostates stimulated, regardless of sexuality.”

“Yeah definitely,” Isaac agreed, arching his hips and grinding down against Stiles’ erection. “But it’s not just that it’s...” Isaac shrugged. “I just know now.”

“Dude, this is awesome!” Stiles said. He tilted forward and gave Isaac a sloppy kiss, then rabbited his hips a few times, making Isaac moan against his mouth. “Welcome to the team.”

“So awesome!” Scott leaned in, his face gently pressing against Stiles’ face too as he kissed the corner of Isaac’s mouth. 

“Anything else you wanna try while you’ve got two guys to play with?” Stiles asked, partly teasing, partly hopeful.

“Actually yes!” Isaac declared. “I want to fuck and get fucked like Scott did.”

“Oh you’re gonna love that!” Scott said, his cock and ass throbbing as he thought about how hard it had made him cum.

Scott eased Isaac back on the bed as he shifted from behind him. He lubed up Isaac’s straining, veiny erection then slicked two fingers and slid them into his own well fucked hole. “Which way do you want me?” Scott asked, straddling Isaac’s waist facing him but ready to turn around if requested.

“Like this,” Isaac said, eyeing Scott’s cock again, then stomach, then his chest, then – _yeah, like this!_

Stiles raised his hands from Isaac’s hips to Scott’s chest as Scott impaled himself on Isaac’s erection with one hard, confident bounce. 

“Oh. My. God.” Scott closed his eyes and let his head fall back against Stiles’ shoulder as he rode the waves of sensation erupting in his ass. He ground his hips in slow, satisfying rolls, clenching his muscles around Isaac’s dick every time another spark ignited against his prostate.

“Jesus, Scott! You’re so loose and slippery yet...so fucking _tight!_ ” Isaac exclaimed as Scott’s ass once again took him from a lazy, wet wonderland to a firm, gripping heaven. Isaac thought he was going to pass out from sensory overload when Stiles moaned and started bucking harder into Isaac.

“My ass is so happy right now,” Scott said. He was grinning so hard his face hurt.

“Let’s make your cock happy too,” Stiles whispered into Scott’s ear as his hand slid down from Scott’s chest to his shaft and he began jerking him off.

“Aww, fuck.” Scott reached over his shoulder and palmed the back of Stiles’ neck, eager to reward him with a kiss.

“You like the way this looks, Isaac?” Stiles asked, making eye contact with him before looking away and surrendering to the kiss with Scott.

Isaac drew in a sharp, gasping breath and let it out as a moan, his eyes raking up and down the scene in front of him: Stiles and Scott locked in a sloppy, heated make out session, Scott’s sweaty, muscular body writhing back against Stiles’ chest and _onto_ Isaac’s cock, Scott’s big, swollen dick in Stiles’ hand, Stiles’ thumb teasing Scott’s glans as he jerked him briskly – it was the hottest thing Isaac had ever seen, and to top it off his whole crotch was burning with pleasure as he watched.

Several minutes later Stiles cleared his throat. “And switch!” 

“What?”

“Huh?”

“Come on guys – ADD. I wanna try somethin’ new.” Stiles licked his lips and grinned as he realized what. “Isaac hasn’t fucked me yet.”

“That does sound really appealing,” Isaac said, thinking back to the way Stiles’ ass had looked as he had climbed the stairs in front of Isaac earlier in the night. There was something else he wanted to try too. Isaac’s hand trailed up Scott’s thigh and over Stiles’ hand on Scott’s cock. “And Scott hasn’t fucked me.”

They separated and repositioned on the bed. Stiles got on his hands and knees in front of Isaac and raised his ass in the air. As Isaac reached past him for the bottle of lube, Stiles grabbed his hand. “No more lube. I still feel full of Scott’s cum. It’s enough, use that. Fill me up with a second load, Isaac. I wanna drip with both of you.”

Isaac trembled as he pulled the butt plug out of Stiles’ ass. _Fuck,_ Stiles looked incredible like this. His hole gaped and flared slightly from having been fucked by Scott’s thick cock and then held open by the substantial sex toy. The smooth skin around his hole was a slick, shiny red and plunging his cock into it felt like the most natural thing Isaac had ever done. Isaac felt Scott’s hot, creamy cum coat his shaft and the knowledge that he was inside the most intimate part of Stiles’ body and slicked with the most intimate of Scott’s fluids made Isaac’s cock throb and his chest tighten. 

Scott on the other hand, reminded himself that Isaac had been an anal virgin less than a half hour ago and that his cock was going to be the thickest thing Isaac had ever taken. He reached for the second bottle of lube and slathered his erection generously and likewise slicked Isaac’s ass as he gently fingered him some more.

“I’m ready, Scott. I just want you inside me. _Please!_ ” Isaac whined and took shallow thrusts inside Stiles as he impaled himself on Scott’s finger. 

“Okay, just tell me if it hurts,” Scott said, pulling his fingers away and tapping Isaac’s hole with his glans before cautiously pushing the tip in.

Isaac moaned and bit his lip as Scott slid in further. Goddamn Scott was thick! Isaac felt a burn that hadn’t been present when Stiles had penetrated him. Yet Isaac moaned harder and collapsed against Stiles’ back as he realized that in this context...he liked it. He liked it _a lot._ He could feel Scott sliding into him inch-by-inch and it was unbelievably satisfying.

“Isaac, you feel really tight. Are you sure you’re okay?” Scott tried and failed to keep his tone neutral, tried to hide how much pleasure Isaac’s hot, tight ass was giving him. He didn’t want Isaac to endure it for his sake if it did hurt.

“I am so fuckin’ okay,” Isaac mumbled, snapping his hips hard against Stiles’ ass then rolled back the rest of way on Scott’s dick, impaling himself to the hilt. The sensations shot up his spine and made the tips of his fingers tingly.

“Okay, just remember we can stop as soon as you want.”

“I don’t wanna stop till you cum in me like Stiles did and till I shoot in him.”

Stiles moaned and braced himself for that long, blissful ride. “Sounds like a good stopping place to me.”

Isaac laughed and set a slow, steady pace, bottoming out hard inside Stiles with every in thrust and grinding back flush against Scott’s pelvis with every out thrust. Scott’s arms were around his chest again and his hands were on Stiles’ shoulders, pulling him back as he pumped in. Scott likewise met his back thrusts with quivering, seeking gyrations of his own.

“Harder, please Isaac! Harder!” Stiles pleaded as his temperature rose, not just in his ass but his whole body. Sweat dripped down his back and tricked in hot rivulets down his thighs, adding to the tickling need he felt consuming him.

Isaac grunted and slid one hand from Stiles’ shoulders to the back of his head, fisting a wet clump of hair and yanking his head back as he remembered Stiles’ hair pulling fetish.

Stiles yelped and let out a low, guttural moan. “Fuck yeah! Ha-harder. Harder.”

Isaac tightened his grip in Stiles’ hair and snapped his hips more urgently with every thrust.

“Harder here too,” Scott pleaded, letting go of Isaac’s chest and leaning back with his torso to give Isaac more room to buck between them. Isaac’s silky heat had gone from _good_ wrapped around his cock to _fucking unreal._ Scott could feel his balls drawing up against the band of the cockring, fighting to get in place and unload but being held back deliciously. The delay would make Scott cum harder, but he needed Isaac to take him there. If he tried to thrust too far into Isaac he would restrict his movements and break the heavenly rhythm they had going.

Isaac gritted his teeth and impaled himself hard against Scott. His vision blurred and he felt like he was going to split open as the aftershocks of Scott’s steel-hard dick crashed against his inexperienced prostate and reverberated through his whole body. The burn had become a blissful, pulsing inferno, and it was just as hot on his cock, despite the slippery, wet piece of heaven he was sheathed in. 

“Harder, Isaac,” Stiles moaned brokenly.

“Harder, Isaac,” Scott begged, just as desperately.

Their needy pleas tugged at his chest, had him bucking back and forth between them with reckless abandon, frantic to satisfy them both and also to relieve the blazing snarl of urgency in his own groin.

“Harder Isaac!” They chanted in unison. “Harder!”

As Isaac rabbited between them, his sense of distinction between his ass and his cock blurred until it was gone, until he was nothing but a white heat from the waist down. They were lighting him on fire from both ends and Isaac was as desperate to quell the flames as they were.

Scott couldn’t take it anymore. His balls clenched and his cock quivered violently within Isaac’s tight hole. Then he was flying over the edge, slamming into Isaac’s ass hard and fast and yanking his hips back in a death grip. He didn’t want to stop Isaac from fucking Stiles, from fucking himself, but he couldn’t help it. Scott’s cock had shattered into a million orgasmic pieces and it felt too good not to pump every single one of them into Isaac as deeply as he could.

“Aaah!” Isaac screamed as Scott arrested his forward momentum and winched him back hard, pounding against his prostate a beat too soon and breaking the rhythm in the best possible way. Isaac split open as Scott blasted him full of cum, finally quenching the fire and melting him into a heap of throbbing, tingly goodness. Isaac in turn yanked Stiles’ head back and locked his other hand around Stiles’ waist, holding him in place as gave Stiles the second load he had been begging for.

Stiles was denied his own release as Isaac’s erratic final thrust missed its mark and left Stiles tangled in a knot of frustration as Isaac seeded him. As he dutifully clenched his ass around Isaac and encouraged both boys to get off hard, he realized he didn’t mind that he hadn’t cum yet. He had both their loads now, just as Isaac had his and Scott’s, but Scott was still missing one. Stiles was glad he hadn’t spilled it against the sheets.

As soon as Isaac’s grip loosened, Stiles pulled away and scrambled to the rear of the bed. “Your ass in mine, Scott!”

Scott giggled and panted, head still spinning as he rolled off of Isaac and onto his back. He raised his hips and spread his legs in the air. “Take it!”

“Uhhnn!” Stiles pounded in hard and fast, hammering Scott’s loose, well-fucked hole with a single minded focus. Nothing mattered but untangling his frustration, relieving himself inside Scott. “Fuck fuck fuck fuck fuck, I need to cum!”

“Do it, Stiles, cum for me!” Scott chanted, grateful for Isaac’s soothing touches as Stiles pounded him.

“Mmmm, oh here I go!” Stiles buried himself as the tangled knot finally unraveled and he erupted in his second, even more powerful orgasm of the evening, shaking and cursing against Scott’s body as Scott’s strong thighs held him snuggly in place.

“There you go, Stiles, there you go,” Isaac whispered, leaning over Scott and pressing his forward against Stiles’.

After everyone had caught his breath and Isaac and Scott had taken off their cockrings, Scott wrapped an arm around each of his friends and laughed as he surveyed the wreckage of his bed. “I’m gonna need to sleep with one of you guys tonight.”

Isaac nuzzled under Scott’s arm and reached across his lap to take Stiles’ hand. “Or maybe both of us?” he asked hopefully, still craving the closeness.

“Yeah.” Stiles squeezed Isaac’s hand and placed a soft kiss on Scott’s lips. “Let’s go shower, then we can all sleep in my bed tonight.”

They all started talking at once as they got off Scott’s bed.

“So this was great!”  
“I had a lot of fun tonight!”  
“I love you guys so much!”

They laughed and exchanged hugs and chaste kisses before heading down the hall to the bathroom and cramming themselves into the shower. It was almost impossible to move and they had to wash each other by necessity due to the restricted space. No one minded, however, and mid-way through things devolved into an all out wet, naked, vertical cuddle session.

Once they were done they piled into Stiles’ bed with Stiles claiming the middle position and the other two wrapping themselves around him. 

“So when you come out to Mom and Dad about being bi...maybe don’t mention _exactly_ how you figured it out?” Stiles said to Isaac.

“Oh really? I was going to lead with the ‘while I was fucking my brothers’ part of the story,” Isaac answered, smirking at him.

Scott shrugged. “They may not care. We’re adults and we’re not biologically related.”

Stiles and Isaac exchanged a look and burst out laughing.

“Not everyone’s as sexually evolved as you are, Scotty,” Stiles said, rubbing his side. “There are some things people should keep to themselves.”

“Oh, you’re one to talk,” Isaac remarked.

“What’s that supposed to mean?”

“It means if you were a super hero, you’d be Super Over-share Man.”

“Would not!” Stiles answered, sticking his tongue out, because Stiles was a paragon of maturity.

“Would too!” Isaac and Scott countered in unison before launching a coordinated tickle attack on Stiles.

By the time they were done wrestling and play-fighting, Stiles’ bed was almost as wrecked as Scott’s.

“So,” Stiles said, still trying to catch his breath as he looked between them mischievously, “race you guys to Isaac’s room?”

Scott and Isaac looked at each other and shrugged, letting Stiles dash out of the room without them and ‘win.’

“You know, I think I want ice cream,” Isaac remarked. “Do we have anymore ice cream?”

“I dunno,” Scott answered, sliding off the bed. “We should probably go check.”

**Notes for the Chapter:**

> I hope you guys enjoyed the final chapter of this smut series. Oh and guess what? This wasn’t just a college AU without supernatural elements, it was also an AU where no STDs exist. We don’t live in that world so play safe, get tested regularly, and make informed decisions.
> 
> Also, if you liked this smut series, keep an eye out for a possible new one I’m considering writing called “The Invention of Sex” in which Isaac and Scott live in a world where sex, sexuality, and physical attraction have never existed, yet they find themselves inexplicably feeling it for each other and have to work out the mechanics of how to have sex without any frame of reference. It’ll be a smut/humor combo with plenty of quirky, absurdity. It’s very loosely based on the premise of the movie “The Invention of Lying” but obviously with sex instead of lying being the thing.
> 
> I’m also considering an Isaac/Ethan/Aiden AU threesome story (ideally only one part, but that’s what I planned for this fic, so who knows?) called “Two for the Price of One” in which Isaac picks up Ethan at a bar, only Aiden’s over-protective and worried about his brother hooking up with a stranger...so he just has to join in to keep an eye on things ;-)
> 
> Just tentative plans though, I may not do either story. In the meantime, please consider checking out my main Teen Wolf serial, [“Iron Claws and Fragile Hearts”](http://archiveofourown.org/works/8091622/chapters/18542080) for a more plot-heavy romance story featuring an Isaac/Stiles & Isaac/Ethan love triangle set against a backdrop of supernatural danger.


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